Another work conference, another new city.
New York City this time.
I’ve been so close to it all my life, growing up in upstate NY, but I have never made the trip in. Never really wanted to. I can’t stand large cities, as I find it impossible to feel comfortable. Where are all the trees, the fresh air? Why is everyone in such a rush all the time?
I grabbed breakfast at a street truck just outside of our conference center. Egg and bacon sandwich with a water…if you could call that breakfast. It pained me to order such a thing. Breakfast is my favorite meal and I like to take care of my body, which is very hard to do on these work trips. A woman caught my eye as I waited in line. I don’t know why, but I had to watch her as she went by. She was dressed in a grey pencil skirt and a beautiful flowing red blouse covered by her grey suit jacket. She had a striking beauty to her. She was speaking with authority over the phone to what I assume is a poor subordinate of hers. She had a body like mine, tight and toned and about 5’7…almost 6ft with those heels she wearing. I didn’t care for how she was speaking but she was certainly inspiring to behold. I noticed almost everyone else was looking at her as she moved away.
“Look sharp lady!”, the truck chef shouts out at me, holding out my order.
“Oh, sorry”, as I traded in my cash.
“Enjoy”, he said winking at me. He was cute for an older man. I gave him a flirty smile and a wink back, put my purse away and started walking towards the conference center.
I was still early, so I leaned up against the outside of the building putting one leg up back up on the wall and started eating my poor excuse of a breakfast. To my surprise it was very tasty. He included a gravy like sauce that paired well with the bun it came on. Still a far shot form my normal breakfast routine of mixed fruit, oats and fresh juices and a few pieces of bacon to help keep my sanity.
Music playing in my ear and good food to eat, I stood there people watching to kill some time. It was a beautiful morning in Manhattan, all things considered. Lots of people hustling by me to get to their jobs. I noticed I was getting looks from the pedestrians…mostly form the men. A man that I can only describe as the typical Wall Street type walked by me and eye fucked me from head to toe. He didn’t even bother looking back up at me as he passed by. Just a sly smile as he lumbered down the street. I loved the feeling of men watching me like that. It was a major turn on for me, to be watched and wanted. I’m guessing he wasn’t concentrating on my outfit, even though it was on point today. Knee-high brown leather heeled boots, tight blue jeans, a tight brightly colored floral designed blouse and a thin black wrap to go around my shoulders to protect me from the morning air. I didn’t really fit in with the business crowd on its way to work. It made me think of the woman from this morning. I wonder if she gets turned on like I do when people watch my every movement. By the amount of people rushing through the doors, I could tell it was time to go in.
Another boring conference…You would think a bunch of doctors would be able to put on an interesting performance but apparently that’s too much to ask for with all of the brain power in the room. I thought as I rode the elevator up to my hotel room. At least they pay for nice places. I admired the mirrors and the gold trimming in the elevator as it zipped into the air. I took a few steps over to one of the mirro panels to check my makeup and outfit and the elevators doors opened. 20th floor, a handsome man in a hotel uniform was standing with a cart waiting to get in.
“Please, after you ma’am.” He said with a bright smile. He couldn’t have been older than 18, but he was quite handsome for a young man. Cute face, broad shoulders, strapping in his uniform. I paused for a second before having some fun.
“Well thank you sweetie.” I said it with a flash of flintiness and looked him up and down slow enough for him to notice.
“I that room service I smell?” I asked him as we traded places.
“Uh yes it is…the steak I believe. Ma’am”. He stumbled on his words.
The doors tried to close with him now on the elevator, but I stopped them. I took a step back toward the elevator and grabbed the other side of his cart. I took a peak under the covered plate a french fry and ate it looking at him without speaking for a moment. The doors tried to close again, but there were again stopped by my hands.
“Maybe I’ll see you later….” Pausing for his name.
“Todd, ma’am”.
“I’m Amanda, room 2078.”
I took a step back and the doors closed at the perfect time. The last thing I saw was Todd’s nervous smile. I can’t be the first older women to hit on him, I thought to myself. It’s possible he didn’t even realize I was 48 years old. I have always taken care of my body and I had great genes. My mother is Jamaican and my father is Irish. I inherited her huge tits and ass and his skinny frame. My skin was a perfect multiethnic blend of color and my eyes are a bright amber color. The other day, a coworker guessed that was in my early thirties…close enough I said.
As soon as I got in the room I had to shower off. Being in the city and around a bunch of people made me feel so dirty. It wasn’t a long shower, but my thoughts were filled with Todd. Not that he was anything special, but because he represents one of my favorite fetishes. I loved younger men and Todd is now in my sights. I will have him inside me by the end of the night, I thought to myself.
It was 7:45pm by the time I finished showering. I came out of the room and was struck by the beautiful sunset view in my room. I was completely naked and stood at the window admiring the view of the west river, through the towering buildings. How many people can see me right now? I wondered. I was up high, but this is New York, there were 10 buildings around me that seemed to pierce the sky. I reached for the menu and called the front desk.
“Hi, can you have Todd bring up an order of the steak and a bottle of wine?”. I liked the idea of ordering my man with my food.
“Yes, right away ma’am”.
When we hung up, I realized I had to plan my outfit.
I opened my suitcase to see my options. I pulled out my black stockings and pulled them all the way up my legs, stopping just below my ass.
I put on the garter belt along with my shiny black thong.
The bra was black lace and see through and could barely contain my chest. My heels were 6 inches of black beauty. I put the hotel robe on over my outfit and did my hair and makeup until I heard the nock on the door.
I closed my robe and opened the door. Todd was standing there with his cart of my ordered items.
“Hi Todd. Come on in.” I gestured for him to enter the room, my robe very loosely fitting.
He could barely take his eyes off of it.
He came in to the room and pushed the cart over toward the back of the room. I purposely left my suitcase open, which had a number of sex toys and underwear out for the world to see.
I followed him to the back of the room and untied my robe. He did some final prepping of the food and wine.
“Do you mind signing this for me?” he said without completely looking back aat me.
I took the bill but I didn’t give it back right away.
He finally turned around and nearly knocked over his cart, he jumped so fast.
I was standing there with my robe still on, but completely open with the bill half stuffed in the front of my thong.
“I can’t decide how much tip to leave”…I said taking a few slow steps toward my boy.
“Maybe you can help me figure that out.” I asked him, now grabbing his belt loop.
“I, I should really get back down to the desk, we are busy.” He said nervously. I was running my hand across his ass.
“That’s fine, I will let you out when I’m done with you.” I explained to him.
“Okay, but I’ve never…” he trailed off without finishing his sentence. After an awkward pause I ask, “Shhh. Am I your first sweetie”? Our lips now an inch away.
“Yes..” he quivered. He instinctively put his hands on my hips and started slowly moving them.
There was no more protest from Todd, but he seemed to be cemented in place. I grabbed him by his shirt and pulled him in to kiss me. It turned me on to know that I would be his first. I would also be setting the bar pretty high for all other women to follow.
I pushed him on to the bed and dropped my robe. I crawled on top of him slowly and took a long feel on his package. Todd has been holding out on me…I thought. It felt big. Bigger than most I have had actually. He has started kissing and sucking on my neck. I grabbed him by his hair and snapped his head back to the bed. I reached back and undid my bra letting my tits fall out. Todd was transfixed. He started to rub them and grab them. I could feel him getting hard against my ass. I grabbed his hands and pinned him back again, slowly lowering my tits onto his face and mouth. He instinctively began taking turns on each tit with his mouth. Leaving behind saliva each time.
When I grew bored, I put my hand on his neck and pushed down, letting him know I was ready to move on. I stood on the bed above him and lowered my thong down. I took one leg out at a time and threw it aside. I was already pretty wet but I wanted him to remember me by taste as well. I took a step forward with each food on either side of his head. I sat down on his chest and put my knees back on the bed. I slid forward, grabbed a fist full of his hair, and guided his face to my pussy. His tongue felt waves of pleasure through me. He had no idea what he was doing, but his exuberance was exciting to me. He licked me all over my pussy and even stuck his tongue inside me a few times. When he started to fall in to rhythm, I leaned back and grabbed a hold of his cock through his pants. It must have been 9 inches at least, probably longer. I was excited to start using him.
With one hand, I undid the front of his work pants and slid his zipper down.
“Pull your pants down.” I said it firmly and in a whisper.
He reached as far as he could pushing them without being able to move the rest of his body. He got them away from his ass but his cock was still partially covered.
“Stop”. I demanded. He stopped moving completely.
“Keep eating me”. I demanded again.
I reached back and stuck fingers down each side of the exposed base of his cock to play with him. Then, I reached and pulled his boxers the remainder of the way off. Once his cock was freed, it shot to its upright position.
I grabbed his head and pulled him away from my pussy. He had fluids all over his face.
“You’ve been holding out on me, this is a nice cock”.
“Thanks, he said with a smile”.
“Thank. You. Ma’am.” I corrected him, demanding that he repeat.
“Thank you ma….” He was unable to finish because I had jammed his face back in to my pussy.
Leaning back, I grabbed my first real handful of this huge dick. It was warm and already very hard. I saw some precum at the tip already stringing out of the top. I slowly moved my hand up and down, jacking off my room service boy. The bubble of precum grew even big with every pump until it started running down the side of his dick. I stopped and gathered some of it up on to my fingers and stuck it in my mouth. I could see his eyes on me, watching me suck on my own fingers. I suddenly felt a build up inside me, telling me I was ready to cum. I pulled his head back and told him to spit on my pussy. Todd shot a huge wad right on to my clit and started to drip off on to his neck.
“Suck on my clit”. As I put his face back to work.
He started sucking and licking on my clit until my legs started to clamp and shake around him. I pulled lifted and jolted as I started cumming. My cum started gushing out as Todd continued to suck, soaking his mouth and neck. I grabbed his hair back again and continued had him watch me convulse as my orgasm came to an end. His eyes were wide with excitement and surprise.
“Mmm thanks baby.” I told him. “Now it’s my turn.” I spun off him and got on all fours on the bed, facing his cock. My ass was pointing straight back at him.
I hovered above his cock and spit down on to it before taking him in as far as I could. I could feel him tighten in surprise. I began bobbing up and down with just my head, sometimes pausing to lick around his enormous cock head. I stopped and looked back at him.
“Play with my ass and pussy while I get you ready”. He was ready now, but I just wanted to feel his hand on me, which have been pinned down where I’d left them for the last 5 minutes.
I went back to sucking his cock, this time using one hand to jack him off and play with his balls. I could feel his balls tightening, so I would need to stop soon if I wanted to feel him inside me. He started with one finger in my pussy and then put one in my ass at the same time. He knew what was coming. Meanwhile, I was falling in love with his cock. I needed it inside me now.
I stopped and looked back at him. “I’m going to fuck you now..” I told him.
“Ye, Yess, ma’am”.
I spun around and straddled him. His cock was folded forward under my soaked pussy.
I grinded up and down a few times before sliding on to him.
He filled me up. I felt impaled, but I needed more.
I grabbed his hands and put them on my hips. I started bucking and moving my grinding my hips on him.
Soon, I was moving fast, up and down on his cock. He was transfixed on watching his cock go in and out of me.
I put one hand on his neck and tightened my grip enough to get his eyes to meet mine. I could tell he was getting close by how he felt inside me. The sound of my ass clapping down on his lap was getting me close to cum again. I knew if I started cumming, he would follow me. I was not done with him.
With no warning, I jumped got off of him. His cock slapped down on to his stomach. He looked at me longing for more.
“It’s your turn to take charge now Todd”, I whispered to him.
“How do you want me?” I asked. He finally go the nerve to get off of his back and stand up.
I looked at him on my knees still on the bed.
He reached out and pushed me over on to my back and followed me on to the bed.
He reached down and grabbed his cock and pressed it against my pussy.
Todd shoved his huge cock back in to me we such excitement that it hurt me.
As I let out a gasp, he put his hand on my neck and pinned me to the bed.
He started fucking my brains out. I could hardly think with him pounding me and chocking me.
Hardly a minute had passed before I felt myself ready to cum. It started without warning and lasted longer than I had expected. I started moaning and gasping as I came on his cock that was going in and out of my pussy. I could feel my cum shooting all over my legs and down over my asshole. I miss judged Todd’s strength and he was able to fight through my convulsions without stopping his attack.
As I regained some of my senses I opened my eyes and saw (and felt) that Todd was ready to explode.
“Pull out and cum on my face.” I gasped through my pinned through.
Seconds later Todd ripped his cock out of me and straddled my chest. I grabbed his cock from him and started jerking him off. After only a few pumps, he shot his load. Spirt after spirt came out on my face, in my nose, my hair, my mouth and down on to my neck and tits. He absolutely covered me with cum. I told him to grab his phone and take a picture of me.
I laid there almost paralyzed as he rummaged through his cloths and took a picture.
“O…okay, done ma’am”. He said nervously.
“Okay, now get the fuck out of my room and come back tomorrow night with more food”.
“Yes, ma’am” he said nervously as he rushed to get dressed. He was out of my room in seconds, leaving me a soaked, used mess on my bed.
It took me a few minutes to regain the strength to move to the bathroom. I could barely open my eyes with all of the cum on my face, but what I saw in the mirror reflected how I felt. What can I do with Todd tomorrow night….I thought to myself. I already miss the feeling of his cock inside me. I jumped back in to the shower and washed off all the fluids. I tore off the comforter for the bed that had just as much cum on it, as was on me. I laid down in exhaustion without putting on cloths. The alarm went off and just like that it was 8:30am and I had a second conference to go to….
