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 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 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&B station and sat back down but I made sure to brush my hip against his arm before taking a seat.

I wanted him so badly, but I knew I couldn't make the first true move. He had to do it, I had to know he wanted me in that way. But I was determined at this point to turn him on so much that he couldn't resist himself. I also brought a little blue pill to assist. I wasn't sure if I should give it to him, I struggled with the idea for the days prior when I got it from a friend. But I crushed it up the night before and when he went to the bathroom I refilled his wine glass and put it in his drink.

We moved to the sofa in the room and we started watching TV, changing channels often until he said he wanted to see what movies they had on demand. I switched to the on demand channel to view the menu. It had every category imaginable. Comedy, drama, action, love stories, you name it and it was there.

I asked him to pour me another glass of wine, I was feeling real good at this point. He did and when he finished the glass I put the pill in I poured the rest of the bottle into his glass. I asked him as I searched the movies what he wanted to watch, I kept scrolling around and I noticed they also had a few porn channels, mostly softcore stuff but you could rent xxx too. I stopped on one of the soft porn channels and laughed when I said "wanna watch this?" His laugh was nervous so I moved along.

I ended up picking out the movie, I put on Monster's ball starring Halle Berry because I love the sex scene in it. He never saw the film. After an hour of the movie I could see he was uncomfortable and was shifting himself on the sofa. I knew the pill was the cause so I laid my head on his shoulder so I could see if I could get a better look if there was a bulge or not. There was.

The sex scene came on and now I was the one shifting uncomfortably. The movie ended and the sexual tension was thick in the air. I said I wanted to watch another one and I flipped thru the channels and left it on a soft porn channel. I got up acting like I didn't realize what I stopped on and told him I was going to change into pajamas. We were both still dressed from the night.

I quickly grabbed and slipped a pair of pajamas, leaving the bra and panties on underneath. I peeked out the bathroom door and sure enough he was grabbing at himself as he watched the soft core porn movie. I came back in and he quickly grabbed a pillow to cover his bulge. And then said he was going to change too.

He went to the bathroom and the scene changed from the man kissing her breasts to her simulating giving him oral and all I could imagine was that it was me doing it to my son.

I slipped a hand inside my pajamas and I was soaked. I played a little with myself. I realized he was in the bathroom for 10 minutes now and I thought he was masturbating and I didn't want him too. So I kept calling him to come back out and asking if he was alright. My interrupting him worked. When he stepped out of the bathroom it was obvious he didn't finish what he intended too.

He sat back on the sofa and again I leaned on his shoulder once more. There was no hiding the fact that he was erect when a scene with bright lights came on the TV and lit up the room a little. He said his arm was cramping from me leaning on it so I took his hand and put it behind my neck and laid his hand on my shoulder.

After about 20 minutes I was shifting my legs onto his thigh, just short of his bulge, he began to shift as well some. He was hard and I know he wanted to just release himself in the bathroom. The combination of my teasing, the wine, the softcore porn and the pill was making him anxious to say the least.

I was enjoying watching him squirm as he tried to move in a manner so he could rub his own self against himself. He was trying hard to have his cock at least feel his shorts or something.

One scene came on and the couple were fucking, I laughed and said "Damn I remember those days!" As if I haven't gotten laid in forever. The fact was I had sex just two weeks prior. It when I took some pictures of it to leave on my iPad for him to find.

I moved my leg a little higher on him, so close to his bulge and he quickly realized it and stopped squirming. I think he was afraid he might touch my leg with it. I was hoping he would. I told him I was going to lay in the bed, and as I began to get up I deliberately moved my knee up high enough to allow it to brush over his erection. I heard a very faint sigh.

I got on the bed, propped up a pillow and watched the film from there. Once more I went to the bathroom, I was literally in heat. I never had to work this hard to get a man to just take me. But this was a different case obviously. I pinched my nipples to make them hard, I wanted him to see them in that state just like in the pool. I came out and he quick removed his hand from inside of his shorts. I knew he was stroking himself. I pretended like I didn't notice it.

I got up on the bed and laid in the middle, I wanted no distance between us when he got in it. I left no choice for him to hide at one side. I started commenting more about the movie, saying things like she's not that pretty, she's not very good at what she's doing, and it was lame acting etc. I was suggesting without saying it that I was better in bed.

I told him I was really feeling the wine and asked if he was too? He said "yeah" I told him to get in bed so he doesn't fall asleep on an uncomfortable sofa. I got up to use the bathroom, not because I had to, I did it because I knew he was hard and I didn't want him to feel embarrassed when he stood up. I exited quickly after making my nipples hard again and laid right beside him.

I was over acting my drunkenness', again being touchy feely, and rubbing my knee up and down his thigh making sure to get dangerously close to his cock every time. I said the movie was so lame and I'd sooner watch the real thing instead of this stupidity. He said really? I said of course! At least you know they're actually doing it!

He said "Yeah right, you're kidding." I said no I'm not and got up grabbed the remote and proceeded to rent a real porn movie. I found one titled "Pirates" I had watched it before and knew it was filled with great scenes.

I really wanted to watch a mom son video but was hesitant to search for the one name "Taboo" A movie I hold close to my heart. It was the first family porn I ever watched and I love Kay Parker. It's why I call myself Kay on here.

He was shocked when I called his bluff and I said "See I told you!" I got back on the bed and I said you're lucky you didn't bet me money! He kept saying he couldn't believe I put it on. I nervously laughed and said lets watch a little of it as a joke and we'll turn it off and go to sleep.

The film started soon after the opening credits and he suddenly had gotten quiet. I was fearful that I may have pushed it too far until I saw his bulge again. I snuggled up against him and resumed my knee rubbing on his thighs, and every few minutes I made sure to bring it high enough to touch just the base of his balls. What was suppose to be a few minutes was now almost 20 minutes, I started breathing heavy when I saw him taking deep breaths, I was letting him know I was turned on also and in tune with his desire.

One scene came on and I said out load that the man's cock was nice looking. I wanted him to know how much I liked cocks and said it about the other men as well. He was breathing heavier. I began rubbing my knee up and down his leg a little faster. Increasing the pace when there was something going on in the film that I liked watching and slowing down when there was no action at all. It was obvious as to what I was communicating to him without actually saying it.

A blowjob scene came on and I began to rub my knee on him again at a little faster pace. I accidently and without thinking said out loud "That's hot!" And he said yeah. I asked him if he liked when his girlfriend did it for him and he said yes. He was giving just one word answers.

I brought my knee up and went higher past his balls and rubbed his hard cock that was now laying firm against his stomach. He let out a sigh and I stopped and left it on it without moving it, I just let my leg from the knee down lay on it. He slowly pressed his hips against my leg. Trying not to make it obvious but he was so horny at this point I dont think he realized how obvious his little movement truly was. So I slightly pressed back my leg down on it.

He was rock hard.

I really needed and wanted him to make the first move but that's all he would bring himself to do. Every so often he would press it again my leg and I would press back right after. We were doing that for a half hour before I reached down and with my finger tip started to rub the head of it. He let out a soft moan and so I continued.

After some of this soft touching I noticed he had closed his eyes. It was apparent he was enjoying my touch more than the porn movie. That was all I needed from him at this point and so I started to rub it up and down with my palm, pressing my hand down on it as I went.