Chapter 3: The Hotel Room

It was freezing as you would expect for Pittsburgh in February so we quickly crossed the walking bridge over the road and got into his car. I really wasn’t sure what was next but he headed to nearby Station Square and after the brief ride pulled up to the Sheraton where the valet opened my door and let me out. Greg gave him the keys and the valet look back at me with a bit of a question in his expression. I was obviously not even eighteen and with the dress I was wearing there was only one reason the two of us would be spending the evening in a hotel room! It turned out that Greg had checked in earlier before he picked me up so we avoided the clerk at the desk and any questions he might have. At least that’s what HE told me at the time and I naively believed a boy his age would be able to book a room at a Sheraton Hotel. In the same confession years later my dad told me he actually hade made the reservations and even checked in to get the keys so there would be no worries about anyone questioned two kids checking in.

Given ht already had the key, we went straight to the elevators and up to our floor. We stood there holding hands as the elevator ascended, another of us knowing quite what to say under the circumstances. We actually had not said a word to each other since pulling up to the hotel and Greg hadn’t mentioned even going to one before so it was sort of surreal to be heading to a hotel room together. Wow, this was going to be the first time I would be in a hotel room without either my mom or dad with me. Greg finally broke the awkward silence and leaned over to kiss me gently.

“I know we haven’t discussed this but I didn’t think there would be a problem,” he said in a soft, husky voice, “If you don’t want to do this just say so and we can leave right now.”

OMG, like I was going to say no? I stood up on my ties and put my arms around his neck and then let one hand slip down between his legs where I got a handful of his balls and cock and gently squeezed them. Show, he was still a bit erect and I knew it wasn’t going to take much to push him over the edge.

“You know how I feel about you Greg,” I whispered back to him, “Don’t worry, I want to.”

That was all we said from that moment until we got to the door of our room. Despite my horniness and the sexual lust I’d been feeling for Greg all evening, I still felt a little tense as he put the key card in the door. I’d been fucked in a lot of places by a number of guys but this was the first time a guy had brought me to a hotel room for the explicit purpose of having sex with me. Was this how it felt to be a hooker? Of course Greg wasn’t paying me, at least not in cash, but in a way what was the point of the dinner really? Wasn’t that actually just his way of “paying” me for what he really wanted from me tonight, to fuck me?

OK, I was under no delusions boys like Greg dated me for my witty conversation and bubbly personality. Like every guy I’d ever dated, Greg really wanted me for just one thing - sex. It wasn’t that I minded, what else would I expect from a teenage boy? Even if I dated a guy who I didn’t have some form of sex with, even if just masturbating for him to watch me (which were few and far between), I still knew from the looks Greg gave me and the bulge in his crotch he wanted me - badly. It was different tonight for some reason, like I was making a transition of some sort although I wasn’t quite sure even what it was.

Greg had to enter his card a couple of times before the light would turn green on the door and he was just about to give up when an older guy, looking like your typical businessman staying at yet another hotel, stepped out from the room opposite ours to head down the hall towards the elevators. He took a good LONG look at me and then at Greg and I could have sworn he winked at Greg. Horny old bastard was probably wishing it was his room I was trying to enter!

Greg finally got the door open and we slipped inside. It wasn’t anything special, a couple of queen beds, a small table, and a dresser with a TV mounted on it. On top the TV was a guide for the in-room movies and a remote. Before we got in any further the bathroom was right by the entrance and suddenly I felt this tremendous urge to pee. Feeling like a little girl, I told Greg I needed to use it and closed the door behind me. I didn’t mind my parents watching me use the bathroom but I was raised with enough modesty to where I didn’t want my boyfriend to watch. In addition, although I liked sex I wasn’t THAT kinky. If Greg had thoughts of doing anything in the bathroom with a guy other than maybe showering together or using the sink-top he could forget them. Such things were totally off limits for me.

Then I noticed there was a robe hanging on hook mounted on the back of the door so I slipped my dress up over my head and kicked off my heels. I loved the way the heels made my legs and butt look but dang it they made my feet hurt! It seemed a shame in a way that I wasn’t able to make use of my bare ass under my dress to tease Greg in some way but I knew someday I would get another opportunity with him or somebody else. Sitting on the toilet I felt that intense sense of relief which comes when your bladder is about to burst and you let loose that first gushing flow of pee. A big sigh erupted from me and I put my hand to my mouth as I didn’t want Greg to think I was starting anything without him!

When I was finished I washed and checked myself out in the mirror. Hmmmm ... I debated the robe. On one hand it would be sexy to leave wearing nothing but I nixed that idea. Then I WOULD be a hooker for crying out loud! Instead I wrapped the robe around me. It was huge and came down past my knees and completely covered me. The terrycloth felt good though and I wondered if Greg would let me take it home. One more look in the mirror and I took a deep breath and let it out slowly, my cheeks filling with air as I released it. My hands lifted up my air and fluffed it out over the robe and I was as ready as I ever would be.

Stepping out into the room, at first I didn’t see Greg. It didn’t help the lights were all out but for a small lamp by the table. As I moved in farther my eyes adjusted and I saw he was already in bed under covers. One look at the chair with his clothes draped over it and I knew there wasn’t anything under the sheets but him! He had the TV remote on the table next to him and was looking through the movie guide. Suddenly a funny thought ran through my head. I’d been fucked a couple of times in a movie theater and in fact had given my first blowjob in one. It was almost as if tonight I was in a private theater with all the room and comfort I had dreamed of during those cramped times when we struggled to get positioned in the dark. Best of all, it was a clean bed and not some awful sticky movie theater floor!

“Hmmmmmm, is there something on that’s more interesting than me?” I asked coyly.

Greg seemed nervous at first and then realized I was just teasing him. I sat on the side of the bed and took the remote from him. “Let me see,” I said as I scrolled through the guide, “Here’s a nice family film. What do you think?”

Greg laughed and reached up for me. He pulled me down next to him although I was still in the robe and he was under the covers. He hesitated for a second and then seemed to gain courage. “Do you like porn movies Kelly?” he asked hesitantly. “I always thought it would be cool to watch one with a girl.”

If I’d been totally honest I would’ve told him flat out that I didn’t - which was the truth. It wasn’t like I wasn’t familiar with them. Indeed, my dad had an extensive porn video collection and he enjoyed watching them so I’d seen most of them at best once. Although it was obvious they turned my dad on from the way he got himself off as he watched, oddly they never seemed to have that effect on me. My mom and I talked about it and she agreed with me but tried to make me understand my dad’s reaction. In a way it helped me because it helped me to realize why the boys got so turned on when I teased them and flirted with them, even though at times it seemed a little silly to me. It also helped me understand, even if I didn’t like the answer, why men didn’t seem to realize what it took to get me off. Sure I could be brought to an orgasm if a guy fucked me and played with my clit long enough. But for me, and my mom totally agreed with me on this one, a good orgasm was 90% mental and 10% physical.

Some of my best orgasms so far had not been necessarily with the hottest guy or the one with the best “technique”. For me it had more to do with how and where we did it rather than how he touched me. Naughty sex in a theater made me cum much harder than doing me in his bedroom with nobody home. Seeing two people fucking on the TV didn’t do a thing for me because I wasn’t personally involved. Now if I was to watch say my best friend and her guy doing it, THAT would certainly be a different story because I could relate to them. Who knows, hopefully they would ask me to join them even! Simply watching a couple of whores (yes, I consider the guys whores as well in porn flicks) fucking in front of a camera crew on a set wasn’t the least bit sexy so far as I was concerned. There WAS one thing though that porn flicks were good for though. I did learn a few good techniques watching the “pros”! One of my dad’s favorites was a whore called Ginger Lynn. I wonder how many of the boys I’d blown knew how much she was to thank for the incredible blow job I gave them?

So anyway, instead of spoiling his plans I gave him a sexy smile and licked my lips. “Mmmmmmm,” I purred, “you pick one out and let’s watch it together.”

Greg didn’t hesitate, he had obviously figured it all out while I was in the bathroom and he turned on the movie. It had just started and sure enough, two girls were fucking some “lucky” guy. I wanted to laugh but I bit my lip instead. The usual guy fantasy of two girls both wanting him. I liked to be alone with a guy to have sex. Why would I want to share a cock with another girl? I guess it was sort of like porn movies, maybe someday I would just to please some guy just as I was watching this now to please Greg.

Greg turned out the remaining lamp in the room so the only light was from the flickering glow of the TV screen. I laid next to him and his hand began to work its way slowly under my robe. They reached my boobs and I felt him squeeze each one and play with my nipples. A tingle ran through me as my nipples responded and hardened between his fingers. I was on my back with Greg on his side and he took his other hand and started playing with my hair. God I loved that! Stroking my hair was almost better than playing with my boobs. Almost mind you!

To be honest I wasn’t watching the movie but rather closed my eyes and enjoyed the feel of his hands groping me. Even so, he had the volume turned up so I could still hear the soundtrack and the fake moans of the girls filled the room as Greg began to explore the rest of my waiting body. Slowly I untied the robe and let it drape open. I could see my nude body outlined in the dim light and Greg’s hand as he moved it over my stomach and down my side, over my hips and then down my bare leg as far as he could reach. His hand turned back and this time was on the inside of my soft thigh and I jumped as it tickled just a bit. He was almost to my crotch when he gently massaged my inner thigh while at the same time his fingers worked through my hair and played along my ears and neck. I felt so relaxed and comfortable.

Greg threw the covers off of himself and helped my arms out of the robe such that I was now completely out of it, exposed and laying on top of it on the bed. He slid over towards me until I felt his warm naked body pressing up against mine. His teen cock was rock hard and pressed against my hip like a warm thick rod and his hips moved in a slow thrusting motion to make it rub up against me. In response I spread my legs obscenely for him and he took the hint, moving his hand upwards until he cupped my crotch in his large hand. His fingers moved around my wet pussy as his palm pressed against my clit. The feelings coursed through my body and I moaned softly as I felt myself reacting inside, getting even warmer and more moist with each movement of his hand. Neither of us said a word as he fondled and groped me gently.

It was so opposite to the wild scene on the screen where this guy was fucking a woman so hard it looked like he was going to drive himself right through her! In contrast I was loving what Greg was doing to me though, gently touching me and running his fingers through my pussy hair, twisting it in small circles and running his fingertip around my clit. Then his finger began to press harder and work its way between my pussy lips until he found my hole and pushed his finger just a little inside of me. He wet his fingertip and used my wetness to lubricate the rest of my pussy making his fingers glide over my clit and driving me straight to my first climax. My hips surged upwards and I gasped as suddenly my pussy was on fire and my entire body felt like an electric shock had surged through me.