A Weekend Long in Planning

It was the night before the weekend, I was nervous as all hell. My hands were shaking, my thoughts were racing and I was contemplating cancelling the hotel booking. I literally had to take a Xanax to calm my nerves. Once I was finally calmed down I decided I wouldn't cancel the hotel. I had to see if after these two years since accidently seeing his beautiful cock that fateful morning when I walked into his bedroom, and caught him masturbating if I could actually go through with it.
If all the thoughts and times I've spent fantasizing about him in such a raw sexual manner could possibly play out over the weekend. Would I be able to go through with it? Could I possibly let myself go sexually with him if I did go through with it? Would he be accepting to the fact of just taking me the way I fantasied he would a million times already?
I needed to find out.
That Thursday night I decided to sleep with just a pair of panties on, a very sexy pink pair of lace, cut high on my hip and snug on my bottom. It was quite revealing. That's all I kept on, just those panties, I was topless as the day I was born. I left the door to my bedroom open and waited for him to come home from his night out with his friends. When I heard the door to the house open my heart started racing, I wanted him to see me in this form close up with just a little night light on in my room.
I heard him get nearer to my bedroom as he walked down the hallway. He has to pass my room to get to his. I pretended to be asleep, I kept no cover or sheet over me to hide myself. I was laying on my side facing the door, while my back laid flat on the bed to expose both breasts.
I heard him walk by the doorway and thought he never realized or looked in but a few minutes later he came out of his room to use the bathroom and that's when I heard him stop at my door, a bit of time passed and he was still there, I knew he was looking at me.
I wondered if he was excited about what he was seeing and if I made him hard.
He finally went to the bathroom, wasn't in there long then returned to my open bedroom door and again he lingered for about 15 minutes give or take and I heard him walk away. I'd be lying if I told you I wasn't feeling waves of hotness between my legs.
The next morning came and I was awake first, in the kitchen making coffee for the both of us when he walked in wearing just a pair of shorts, I could see the outline of his young cock through the thin material.
He caught me looking. I was embarrassed but acted like I didn't know he saw me looking at it. I asked how he slept and he said "good" I asked is he was packed for the weekend and again he answered yes, I reminded him to bring his bathing suit for the hotel pool and we'd be leaving shortly after breakfast.
My bags were already packed the week prior, I filled it with every piece of lingerie I have, figured I would decide what I'd feel comfortable putting on at night around him once the night time came and we were back in the room. I left myself options just in case.
When we arrived I checked in, he was checking out the lobby and said they had a Starbucks on the corner for the morning. We arrived early and the room wasn't ready for us yet. We had an hour and a half to kill. So I suggested we go to the pool. We took the swim suits out of the bags and the staff was to bring the bags to the room for us while we were at the pool. We changed in a courtesy room for hotel guests. Him in his swim blue swim trunks and me in a yellow bikini.
We got two chairs to lay on and I went for a drink at the pool bar, he asked if he could have one, he's never asked me if he could have a drink before, even though I know he's had some with his friends. He won't be 21 until May. I said ok but only one, he wanted a beer but I got him a glass of wine instead.
After a little time we went into the pool. The water was colder than I thought it would be. It made my nipples' hard and it was obvious, you couldn't miss them pointing out of my bikini top if you tried. You could also see the nipple piercings I wear. I caught him looking this time. I felt a pang in my belly when I saw his eyes glued to them. We swam around for a bit, talked and drank our wine.
The pool wasn't too crowded but there was enough people in it for me to make the excuse to brush against him often or lean my shoulder against his arm. I was touchy feely with him in the pool, touching his arms, his chest and I asked one of the staff to take our picture.
I leaned in close as if I was his girl, I had the person take a few because I like feeling him next to me and wanted it to last a little longer. The last photo I was standing in front of him while in the pool, the water was just at his waist and just some inches higher on me. He has about 5 inches on me now at least.
I pushed my back on his chest and then without thinking about it I pressed my ass on his crotch. He was hard. And I damn near felt my head spin. Did I do that to him? I must've I thought because no one else was on him klasbahis yeni giriş but me. At that moment another employee came over and said the room was ready for us. That moment of sexual tension and heat was cut off. But it left my legs weak.
We went to the room and he realized there was only one bed. It was part of the plan so I acted surprised, I was afraid to say I booked it this way and let me see what I can do about getting a new room. So I fake called downstairs to the lobby when he was in the bathroom getting ready for a shower. I spoke loud enough to a dial tone so he could hear me and I pretended to complain about the one bed.
Finally ending the act with an "Ok, call me if another room becomes available. He came out of the shower with just a towel around his waist, it took all I had not to look down at him. He asked if there was another room with two beds and I said no. We are stuck with this one. He said no worries, it's a big bed anyway. He was right because I got a room with a king sized bed. Again I was thinking ahead just in case I had a change of heart or if he was unresponsive. At least there would be distance between us.
I showered next and came out the same way as he did, with just a towel on.
He asked me if I wanted him to leave for a minute so I could change, I said very nonchalantly "Nah, just turn around for a minute. No big deal" I grabbed my things, a black thong with matching bra. Again lace and again very revealing and form fitting to my body. I made sure to drop them on the bed so he can see what I was going to put on and then took out a black cocktail dress. It fell just below my ass, it's the sexiest one I own.
I told him to turn around and he did, I was slow in putting on my things, I had my back to him and I was deliberately taking my time hoping he would sneak a peek.
I finally slipped on my dress and told him it was ok to look now. I pretended to have trouble with the zipper on the back and asked him to help me. He did, I then sat on the bed facing him in the chair he was sitting in and put on a pair of black high heels with a strap that wrapped around my ankles.
Uncrossing and crossing my legs in front of him just enough to show the panties I was wearing. And I thought oh my god I'm trying to seduce him. I became well aware of what I was doing at that point and began questioning my sanity, but stopped when I said he'd never make the first move so I might as well have fun teasing him and I would use the situation when we were back home to masturbate to.
He was handsomely dressed in black slacks and a button down baby blue shirt.
We had reservations for dinner at an Italian place called Carmines. The place was louder than I had hoped. I wanted a dark quiet and intimate setting but it wasn't to be. We ate, I allowed him another glass of wine with dinner and we walked the city streets people watching and checking out the sites.
I kept grabbing his hand as we walked, at first I think he was uncomfortable with it but after an hour or so he didn't seem to mind when I reached out to take his hand as we walked.
It was after 11pm when we headed back to the hotel, that's when I saw the hotel bar, it was very dimly lit, not crowded at all, only a few patrons and most were sitting at the bar. I suggested to him that I wanted another glass of wine before heading to bed. I told him he could have one as well since he was with me and he wasn't driving.
We went in and sat down, I ordered for us both and we talked for awhile, I asked him about his girlfriend, and if they were serious. He said no not really, I asked if he wanted it to be and he said no. I was actually happy he said that, I think I was jealous of her.
I told him I was so happy he decided to spend the weekend with his old mom and he laughed and said I wasn't old. It felt good to hear him say that to me, it's true but I'm glad he wasn't looking at me like that.
We had two glasses of wine and I felt a slight buzz, nothing crazy as I love wine and I can have more than two. I had just enough at this point to speak more freely and without inhibition.
The conversation turned more personal, I asked him when he lost his virginity, he turned red and I laughed and said "Seriously, I want to know because I think you were 18 when I noticed a change." He said he was almost 17 when it happened. I was honestly shocked because I never realized it. Too much evidence of him masturbating in the house at that age for me to think otherwise. He said it was a one time thing and it was just some girl he knew from school.
He already knew how old I was when he was born, I was 19. But he surprised me when he asked how old I was when I lost mine. I lied and told him 20. I was actually 13, the boy was 20. I had a huge crush on him. He showed me everything during that summer, we did just about everything sexually too, even attempted anal. But I stopped him. That was something I wouldn't get use to until I was in my later 20's. He laughed and said I was klasbahis giriş a late bloomer compared to his generation. Little did he know.
It was now 12:15 and I asked the bartender for the tab but he said the gentleman had already paid for the drinks. He did it when I went to the bathroom. I smiled and asked if I could buy a bottle of wine for the room and he said he would have them send one up and charge it to the room number. We left the bar and went upstairs to the room. I kept the lights dimmed because I didn't want to spoil the mood.
The bottle arrived shortly after returning. He asked when I ordered it and I said I can be sneaky just like him and I ordered it when he was in the bathroom like he paid for the drinks when I went. He started laughing.

My mind started racing again after the first glass from the bottle, I was nervous, apprehensive and incredibly turned on. I could feel my own heat. I was wondering what if anything was going thru his mind, I was constantly uncrossing my legs as we sat at the little table drinking wine. I got up and turned on some music, I found an R