If you like this story please consider checking out my Patreon at patreon.com/TedDavidson_Writer.
I make bi-weekly content that will always contain gay, bisexual, trans, and sissy content. I also do requests at other tier levels, where you pick the characters and topic, and I made your fantasy a written reality! Also please check out my published book on Amazon. "Snowed In With My Best friend" by Ted Davidson. It's free on Kindle Unlimited!
Thank you for reading!
Please remember to donate to keep stories like this and many many more alive at https://donate.nifty.org/
Chapter 2
Even though I knew that I was gay, I had never had anything substantial in my ass. I knew once I had started jerking off at around 14 years old, I knew that there was something that I was missing. Just looking at some porn that I would find on the internet, I found that guys enjoyed fucking each other in the ass. The thought always blew my mind. I started to explore the idea sometimes when I was in the shower. I would was between my cheeks, but then tickle my puckered hole, dragging my fingers across it, sending shivers down my spine. Then one day, I took the plunge (no pun intended). I lubed up my index finger with a good glob of Sarah's conditioner, and started to press against my entrance. I didn't think that I was going to be able to get it in but then, it slid into my tight hole. My body immediately tensed, and I pulled it from my ass immediately, hurting worse than when I pushed it in. I cringed as the pain started to fade, then decided that maybe it was just not for me. A couple weeks went by. I was extremely horny again, and knew that I wanted to try again. I had stolen a tub of petroleum jelly from the bathroom, and was now standing next to my computer desk, nude. I had a porno playing of two guys absolutely hammering each other. I pulled out a large glob of jelly, then started to spread it around my puckered hole. I decided to try my index finger again, and started to press against my reluctant ass. This time though, the jelly made it less of a fight. My finger slid in with nearly zero resistance. The pain came, but very quickly faded. What I was left with was a very pleasant full feeling, and my finger dragging across my prostate ( I didn't know it was my prostate then) nearly made me blast a stream of cum onto my desk. I withdrew my finger and knew that I needed something bigger. I tried two fingers this time, and they too slid in with no problem. I thoroughly enjoyed the feeling of my fingers dragging against my ring and prostate, but I just felt like I needed more. I searched around my room for something, anything! I saw on the top of my dresser my small, souvenir baseball bat that was given to me at the college baseball game our family went to last year. I eagerly grabbed the bat, and slicked it up with the jelly. I planted one hand on the edge of my bed, and reached behind with the bat. I pressed it between my cheeks, and started to slide it around until I found my mark. I began pushing it against my opening, but it just wouldn't budge. I took a deep breath, and started to relax more, then started to push again. It happened. The tip of the bat slid past my virgin hole and started its slide deep into my bowels. My head shot back in pleasure. I even moaned under my breath. The bat continued to slide until I felt the knob of the handle rest against my ring. The foot long bat was completely inside me. I looked down to my rock hard cock, and noticed that it was leaking pre-cum like a river. I pushed the bat so it slid out, then pushed it back in, but with that last push my cock began to spurt without me even touching it. I shot load after load of sticky, hot cum all over my bed. I was left panting, the bat still completely in my ass. I grabbed the knob of the bat and started to slide it from my ass. It popped out at the tip, then landed on the carpet of my floor. I knew then that I was now a bottom.
After that day, I could not stop trying to find things to test my capacity for size. I would try anything that was round with a tip, even the cucumber that my mom bought for her salads. I needed to try anything that I could find. But none of that would prepare me for what I was about to experience in that room that Brad had just sent me into with a customer named Chris.
I lead the way towards room two. Chris was gripping at my ass cheeks the entire way. I grabbed the door know and looked back at him with a lustful look. A cocked smile and a raised eye brow "You ready?" I said, still not knowing what was in room two, but I sure knew that I was ready. Chris bit his lower lip, signaling that he was. I pushed in the door, and we both stepped in. Before I could even flip on the light, Chris was pulling me around to bring me in for a tongue fill kiss. I danced my tongue in and out of his mouth. He was feeling up my body as we kissed, pulling at my shirt and running a hand inside the waistband of my leggings. His hand would glance across the top of my ass crack which began to send tingles through out my body. I was moaning, lusting for Chris. I was kissing him so long that I would have to stop just to breathe. I broke the kiss to back away from him a few steps. I glared into his eyes as I removed my shirt over my head, then pulled my leggings down to the floor. My skinny frame was now completely nude, waiting for Chris to take his prize.
"Spin for me." Chris said, rubbing at the bulge in his jeans.
"Anything for you, baby." I replied, doing a slow twirl so that he could get a good look at what was his.
As I spun I took a good look around the room. Not a lot changed from one to the other except this room had a bathroom along the right side wall. I wondered if it was just a bathroom, or possibly had a shower too. I felt that after a day of meeting these men, I was going to need it.
I took one more half spin then stopped so I was facing the bed. I bent over to place my palm flat on it's surface. I looked back at Chris, who was starting to unbutton his nice pattern shirt. He pulled it from his shoulders, revealing an amazing body that was completely shaved. His chest muscles bulged as he threw the shirt towards a table in the corner. I gave him a smile, then took a hand to one of my cheeks and gave my ass a good spread, letting him see my hairless, pink ass hole. You could almost see his knees buckle at the site. He bit his lip again.
"You want this, don't you? I said, almost begging him to say yes.
He unbuckled his pants, then let them fall to a pile beneath him. He was not wearing underwear. His cock fell out as his pants fell to the ground. My jaw hung open while I tried to comprehend what I was looking at. His cock was nearly six inches long, and it wasn't even hard yet.
"You want this, don't you?" he grabbed his dangling meat then dropped it, the weight of it made it hit his thigh with a `smack'. I bit my lower lip and just nodded. He walked to where I was still bent over the bed and pulled me to him, his cock pressing against the top of my crack. He was leaning down and sucking on my neck which was causing me to moan even louder. My eyes were closed and I was running my hands along his arms as he started to feel my up again. I was lusting for Chris hard now. I wanted his cock. I needed his cock. I spun the two of us around, then slipped from his arms. I pushed him in the chest, making him sit on the bed. "Lay down on the bed." I said, walking towards his dangling legs. He smiled and climbed the rest of the way onto the bed. He laid back so that his head was on the pillows, and his legs were slightly spread. I climbed up between his legs and took his massive cock into my hand. Gripping it, I could barely reach my hand all the way around it. It pulsed in my hand as it continued to fill with blood, growing more and more. I jerked his cock slowly, waiting for it get a hard as it could, then I started to tease him with my tongue. I met his gaze as it flicked my tongue across the tip of his cock, running it into his slit, the dancing around the rim of his head. I drug my tongue down the length of his shaft, then back up to the tip, where I continued my teasing tickle dance along his tip. He was nearly begging me to take him into my mouth but I was having too much fun watching him squirm. I drug my tongue down his shaft again, then started the dance along his loose nut sack. I licked frantically at his balls as I pushed his cock against his belly. His thighs were trembling against my arm, he was clearly enjoying this. Then, I did something he was most certainly not ready for. I ran my tongue below his bag, then down his taint, landing against his hairy ass hole. I felt his legs stiffen after I hit my mark. I toyed with his ass hole, poking at it with my wet tongue, the soaking it as I laid my lips on it, eating it like it was my lunch. He was trembling again, the joints in his toes were cracking as he curled them. I pressed on with my tongue, trying to make my way inside him, but he was reluctant. I licked my tongue up and down his taint one more time, before going back up to the head, then plunging the rod into my mouth. My throat was already widened from Jim earlier so I was ready to go for Chris, but I was still only able to get about half in my mouth before my gag reflex told me "no more". I held his cock at the back of my throat, cutting the air from my lungs. I was lusting for his cock and wanting it in my mouth so badly, I would have nearly choked myself with it if it meant it would stay in there. I pumped what I could of his meat into my mouth, sucking hard, and swirling my tongue around it. Chris was moaning and I could feel his hips buck beneath me, trying to get his rod further into my throat.
I couldn't blame him, I wanted more of it too.
His cock was now a slobbery mess when released it. I tried to swallow all of the spit that was gathering in my mouth, but it was a near impossible task. I was addicted to Chris' cock. I gave his cock a quick three or four strokes before climbing onto him. I sat on his waist, his cock between my ass cheeks. I leaned into his face, locking lips with him again. He clearly didn't mind that I had just munched on his ass. I reached behind me to feel his wet cock, and started to ride him, grinding his dick with my cheeks. He broke from our kiss to moan loud enough that I'm sure whoever was in the lobby had to have heard him. I smiled down to him, the stopped my grinding.
"You wanna fuck my ass?" I said, trying to lift my voice as high as I could, bringing out the true Jenny voice.
He did not even respond, he just pulled me in for another kiss, which I broke again. I saw on the side table that there was a convenient bottle of lube with a pump top on it. I crawled over his to the table, and dispensed some of the liquid into my hand. I came back so that I was straddling him again. I moved back so that his cock was now pointing straight in front of me. I drizzled on some of the cold lube and started to work it into his meat. I then stood up and looked down to him, I smiled as I reached behind me to work in what was left of the lube into my hole. I started to squat down, aiming my tight hole towards his rigid dick. I placed one hand on his chest to balance myself, then reached under me to guide his dick towards my entrance. I it start to part my cheeks, then press against my opening. I continued pushing against it, clenching my teeth, waiting for the pain that I knew was coming. I gave it one more push and his head crammed into me. I stopped my pressure as the waves of stinging hot fire rippled through my lower half.
"It's so fucking big." I said through a clenched jaw.
"Just take it slow." Chris said, rubbing my hairless thighs, making me feel more relaxed. I took one more breath, and started again. His cock was just so thick! It was like stretching a rubber band over a fire hydrant! My ass was able to take it though because before I knew it, I was sitting on Chris's lap again. I put both hands on his chest, and let my ass stretch more. After only a couple second though, my ass opened up and I was ready for action. My teeth released their tension, and I looked down to Chris.
"You okay?" he asked, still stroking my thighs. I smiled back at him with my crooked smile again, he knew I was ready. I pushed myself from his cock, letting it withdraw to his head, then I eased myself down his shaft again. He began to moan as I continued to impale myself on his steel hard prick. I would continue my slow ride, raising, then shoving it back in for a minute then began to quicken my pace. I was starting to bounce, getting not his whole length now, but enough to drag across my ring and send shivers down my spine. My bounce turned to wildly riding, loving every inch of his cock as it ran into my depths, plunging further than that stupid bat ever could! I loved his cock, I needed his cock. I was obsessing over it even though it was tearing me apart right then! Chris grabbed my hips to help slam me down with every thrust, the pleasure only increasing with every stroke!
"You feel so good baby." Chris said, forcing me down again onto his cock.
"You are so big, your cock is so fucking big." I screamed.
"Oh shit, oh fuck, I'm going to cum!" he groaned. I slammed back down onto his cock so that it was fully inside of me. His hands gripped at my skin as he began to ejaculate into my bowels.
"Jesus fuck." he was bucking below me. I felt his hot cum coat my insides, filling every inch. I leaned down to his panting chest, and gave him one final kiss. I pulled myself from his shrinking cock, it popped from my ass and a little dribble of cum trickled down my leg. I slammed my ass shut, not wanting to make a complete mess on the bed. I climbed down from the bed and stood next to where he was still trying to catch his breath. I leaned over and gave his chest one final kiss.
"I will be back shortly." I ran my hand along his chest. I turned and walked towards the bathroom, I knew that I wouldn't be able to keep his cum inside of me, not while I was wearing black leggings.
Inside the bathroom was extremely nice. There was an assortment of different candles, different toiletries, you name it! There was even a shower!I walked over and sat on the toilet I started to push his jizz from my over worked ass. By the feel of it, it had to have been nearly a cup that was stuck inside me. I wiped myself clean, then walked out to and empty bed and an empty room. Chris had packed up and left without saying goodbye.
I walked out to the lobby where I saw Seth still sitting at the front desk, taking a call. There were no clients waiting so I walked up to the desk to wait for Seth to finish up. He clicked the phone down.
"What's up?' was all he could say.
"Where did Chris go?" I asked.
"He went home, that's what they do when they are finished." He said, sounding like I should already know that answer. He must have seen that I was slightly sad because his tone changed immediately. "Oh hunny I'm sorry, you were falling for him weren't you?" he asked.
"I just, never had anybody make love to me before, he was my first." I said, dropping my head to look at my shoes.
"I'm so sorry! I'll tell you what, why don't we do lunch together, like a girls date?" he said rubbing my arm.
I lightened up a bit at this. "Sure, that sounds great!"
"Awesome! I will drive." he said, grabbing a hand bag, and his keys that were attached to a long lanyard. "By the way, you can call me Kayla." he said, extending a hand to me. "And you can call me Jenny." we shook hands then as girls. Just Jenny, and Kayla. We got into her car and took off.
"I know this bar right down the street, bunch of hot guys there all the time." Kayla said with a chuckle "And if we find one, we can even use the rooms back at work!"
I liked that idea. I gave Kayla a big smile. "Thank you for this."
"It's what us girls do!"
If you like this story, feel free to check out my Patreon at patreon.com/TedDavidson_Writer and also don't forget about my book that is on Amazon. It is titled "Snowed In With My Best Friend" by Ted Davidson.
Thank you for reading!