Dear diary,
I wasn’t prepared for today.. but I did hold my ground.. I flirted with the line and fought back and kept things on the right side.
Last night was…interesting. The one bed was a bit of a jolt, but it was workable.
I had gone to the bed before him and scrolled my phone for a while until he came to bed after his show was over. I figured ‘it’s a big bed, so we will have space’….no. He stripped naked and crawled in to bed next to me.
“I hope you don’t mind.. it is healthier to sleep naked anyways, you know.” He said with a coy little grin.
I shrugged it off and stayed on my side. Then he closed the distance and spooned me, but he used his hand to physically move my top leg back and over his legs. “There we go… this is better.”
He then reached his hand under my shirt and grabbed my left tit. I could feel his dick resting against my ass and realized: I’m quickly losing control of the situation.
“Are you going to press your dick against me all night?” I asked, looking back at him.
“Sorry,” he responded. “You’re right.” He let go of my tit and reached down and repositioned his hardening dick from pressing in to my ass, to in between my legs, resting against my panties.
“Seriously?”
“Shhhh..It’s time to go to sleep, I have a long day tomorrow and want to get an early start.” And with that, he reached his hand back under my shirt and on to my tit.
Feeling his dick against my panties was… a lot, but I wasn’t going to be the first to call chicken and back out. I stayed right where I was and after a few minutes, he was asleep.
Then I realized, as nervous as I was and as adamant that I needed to be in charge… I never moved. When he put my leg on his, essentially giving his dick the room to be between my legs, I stayed still. When he put his dick between my legs, I stayed still. When he grabbed my tit while spooning me, I stayed still. I was losing this war. But still… I didn’t move. And before I knew it, I was out cold too.
Hours later, I heard movement and woke up.
“Good morning sleepy head!” He answered, fixing his tie.
“What time is it?”
“It’s gonna be 6:20 in a minute, I gotta get to the clinic where we are gonna get our CEUs and training done. There’s money on the coffee table in the living room, and I also sent you some cash on your card. Go out and shop, eat or do whatever you’d like, just make sure you enjoy yourself, ok? I’ll be back in the afternoon, then we can go to the pool and relax.”
I thanked him, and hugged him. As we broke the hug, he kissed me. “I’ll see you later.” Then he threw the blanket off me, pushed me down and kissed my pussy over my panties. “And I’ll taste YOU later.”
FUUUUUCK!!! It’s like he knew how to turn me on!!! SNAP OUT OF IT ELIZABETH!! You’re supposed to turn him on!!
He walked out of the room and I laid in bed till I fell asleep again.
At around 12, I woke up and showered, then took an uber to the mall, basically to kill time and window shop unless anything caught my eye.
Eventually, I got tired of walking around the mall and took an uber to a local liquor store and bought a few bottles (it was A LOT) of wine, cuz your girl lovers her some Sauv Blanc. It’s cheap, easy to drink and it gets the job done.
By the time I got back to the hotel, it was around 3, so I went to the downstairs restaurant and got myself a quick bite to eat before heading back up to the kitchen area to refrigerate some of the wine. After lounging around for a bit, I decided to get ahead of the curb and put a nice revealing black bikini on and a long crocheted dress cover up over it, then I waited for him to get back.
At around 4:30, I heard the door open and he finally walked in.
“Holy shit! I’ve been waiting for you this whole time! Hurry up and get changed so we can go to the pool!”
“Well, it’s nice to see you too, sunshine!” He shot back with an equally annoyed and amused tone. He put his bag down and walked to the room to get changed when he saw a few of the wine bottles that didn’t fit in the fridge. “Why didn’t you put the wine in the fridge?”
“Because it didn’t fit in the fridge.”
“What’s in the fridge?”
“More wine.”
“What? How much wine did you buy?!”
“Enough, I got enough..” I sighed cuz I was getting impatient. “Hurry up!”
“I’m hurrying!!”
After a couple minutes, he came out of the room with two towels….and no bottles or glasses.
“What is the matter with you?!” I got up, walked up and grabbed the towels.”
“What? What did I do?!”
“Grab a few bottles!! We’re gonna be in a fancy ass pool, let’s get drunk!”
He laughed “yes ma’am!” He then walked back to the room to get some wine.
“Not those! They’re hot! The ones in the fridge!” He came walking fast out of the room looking mildly embarrassed and made his way towards the kitchen area and opened the fridge.
As soon as he saw its contents, he looked up at me. “‘Enough’?? You bought enough wine to be drunk for 4 days…” He grabbed 3 bottles and put them on the counter behind him and grabbed a couple of plastic disposable glasses that I had also bought. I handed him a tote bag, he loaded them and then we were off.
We got to the elevator and he had such a giant smile on his face.
“Why are you so smiley?!”
“Either Im gonna look like the smoothest player in the world by getting you, or you’re gonna look like an absolute gold digger for getting with an older man.”
We both laughed as the doors opened. We got in and we made our way towards the pool room.
Once we got there, we saw that the pool was very much alone except for a couple of the workers who, I’m assuming, are there to make sure either no one drowns or to clean up after guests leave.
We got our stuff out down next to a couple of lounge chairs and he wasted no time in grabbing my ass. It still freaked me out, cuz… we’re out in public, but again…. No one knows us out here!
I turned to him, with the initial thoughts to tell him to calm down, but as I turned around, he had other plans, and his lips locked on to mine. Instinct kicked in and before I knew it, our tongues were intertwined, tasting each other, my hands on his arms, him with on hand on my hip, the other on my neck. We broke our kiss and he smiled. “Open the wine, I’m gonna get in the pool”
OOOOOOH!!!! Some times I hate that man! HOW?! How can he just shove his tongue in my mouth and then hit the brakes like that?! But it’s fine… it’s fine.. I grabbed one of the wine bottles, opened it, and poured us both a couple of glasses.
Over the next hour, we dipped in the pool, made small talk, drank A LOT of wine and flirted incessantly and made out without any sort of discretion.
After a bit, he got out of the pool and stumbled over to the lounge chair to get us more wine.
“Shit….. Lizzie…. We’re out of wine!” He sat down in the lounge chair, half laughing. “How did we drink it all so fast?!”
“There is no way we drank it all.” I got up and half stumbled over too. “We brought 3 big ass bottles! We haven’t been here THAT long!”
I looked down at him, still shocked that all the wine we’d brought down was gone.
He laughed as he looked up at me, me with the shocked look on my face. “Hey… do me a favor.”
“I’m not walking up by myself to get more wine.”
“No, doofus….” His jovial smile twisting a bit. “Straddle me on this chair and let’s make out.”
“I’m not going to straddle you!”
“Don’t be a wuss, mija! You have a bikini on and I have swim trunks! It’s not like it’ll slip in.”
“We’re in public….”
“Don’t tell me you’re STILL scared?! You sure you my [redacted]? Cuz I feel like my [redacted] is fearless.”
“Don’t. I’m not afraid!”
“Prove it!”
“Fine!” I growled at him and threw a leg over him. Won’t lie… almost fell and broke my neck when I was on one foot, because…wine. But I did manage to straddle him. “Do I look scared now?!”
With that, I leaned forward and shoved my tongue in his mouth. Our tongues dancing, rubbing on each other. I felt his hands reach for my ass, squeezing it as we kissed. I moaned in to his mouth as he squeezed on me. Without thinking, I started gyrating my hips on his, rubbing my bikini class pussy on his dick behind his swim trunks. I could feel his hard dick, trapped beneath me, rubbing against me. It had me so fucking wet. We kept making out.
Between his hands on my ass, my pussy grinding on him, and his lips and tongue on mine, I completely forgot we were still by the pool until I heard a voice saying “excuse me!”
I broke our kiss, stopped grinding and looked up. Standing to the side of us was this woman in a hotel staff shirt looking mildly uncomfortable.
“We’re so sorry! We’ll stop!”
She shook her head “No, we’re sorry, but we can’t have you two doing that out here. We appreciate you wanting to stay at our establishment and take advantage of the pool, but it may be more appropriate if you two were to move your displays of affection to your room, please.”
He responded. “I’m so sorry! It’s just.. look at her! When you mix wine with company that has body like that, these things happen, we’re heading back to the room. We apologize.”
Now I was back to being mortified. But there he was, talking us out of the situation.
“No, absolutely, sir! I totally get it.” The lady continued. “Who would be able to keep their hands off her, given the opportunity!”
He laughed, I blushed and got off him and we started gathering our stuff, including the trash, but we were quickly stopped.
“No, no, don’t worry about the trash, we will take care of that stuff for you guys. Just make sure you get all your stuff, towels, phones, bags, clothes, shoes, etc.”
Once we were packed up, we went back to the elevator and I won’t lie… I was kind of embarrassed. Him? Having the time of his life!
“Well, the pool was fun, wasn’t it?!”
“That’s so embarrassing!”
“Why?! She thinks you’re hot!”
“We were dry humping in public like drunken idiots!”
“Yeah… like hot drunken idiots..”
I looked at him and cracked up. Embarrassment: gone.
We got back to the hotel suite, and he held the door open for me. As I walked in, he spanked me really hard. FUCK…. I love that…. As he walked in, I turned to look at him. “Take your swim trunks off and go sit on the sofa.”
He looked taken aback, but a big smile came across his face. “Yes ma’am!”
He took his swim trunks off, and ran to the sofa naked. I walked over and saw him sitting in the middle of the sofa, smiling, waiting to see what was going to happen.
I got in front of him and squatted down between his legs.
“Ok… I have a gag reflex… but I want to try and more of your dick in to my mouth.”
“….wow.. do you want me to help?”
“ABSOLUTELY NOT!” I looked at him with a real serious look on my face. “If you push my head down, I’m going to bite your dick, understand?”
He laughed, but nodded.
With his acknowledgment of understanding, I lowered my head and took his dick in to my mouth. He gave an immediate gasp as he felt my tongue glide down his dick and I warmed myself up, making sure to make his dick as wet as possible, thinking that with more of my saliva, it would act as lube and help me slide his dick in to my throat.
I bobbed up and down on it slowly, making sure to rub my tongue on as much of it as possible. But every down slide, I tried to get more and more of his dick in to my mouth. The problem as more of it went in to my mouth, the more I had to fight gagging, until I made a a big dive and I gagged. My back flexed, my mouth opened wider, my tongue tried to hit the roof of my mouth, but hit his dick, and I pushed myself off his dick by pushing off his thighs with my hands.
“Fuuuuck…”
I coughed and could feel the tears start to well up in my eyes. “Damn it!”
“For what it’s worth, Mija… that felt good…”
I gave him a judge-y look and went back to sucking his dick. Up and down I went, rubbing my warm wet mouth on his rock hard dick. Again I went lower and lower and lower, each time getting a deeper and deeper moan from him.
I slowly steadied myself and then tried again, pushing myself as far down as I could, and again, I hit my limit and I gagged HARD.
I don’t know if this happens to everyone, but when I gag on something, my body almost panics. Again, his dick still in my mouth, my back flexed, pushing myself head forward, and it took a second before I pushed myself up off his dick. But as soon as he felt me gag and felt my tongue push up, he flexed too, and gasped/moaned.
I went back to coughing, my eyes welled up again. “Fuck! I can’t do it..”
“Fuck, baby… get back to sucking… I’m so close, I don’t need to be in your throat mija, I just need to be in your mouth..”
I understood the assignment, and immediately put his dick back in my mouth, but used my hand in tandem. As my mouth slid down his dick, my hand stroked down on it. As my mouth slid up his dick, my mouth came up with it, until I could hear his breathing quicken.
At that point, I locked my lips on the head of his dick and used my tongue to flick the underside of the head of his dick, each flick getting a nice little jerk from him, and I used my hand to stroke the rest of his dick.
“Fuck! I’m cumming!”
Pop….pop….pop….pop… 4 strong jets of his cum flew out of his dick, coating my tongue. I kept stroking him and sucking though. His hips bucked up, and he moaned like almost in a painful sort of pleasure, but I kept on, until he physically stopped me.
“Fuck! Ok! Ok! Ok, mija! I’m done!” He grabbed my head and pulled up, getting my mouth off his dick. My lips clamped as soon as his dick left my mouth, and I looked up at him, his cum still in my mouth, and swallowed it. His body relaxed and he slumped in to the sofa.
“Did you enjoy that?”
He nodded. “Yeah.. very much so..”
I stood up and walked towards the room.
“Where are you going?!”
“To shower. I still smell like pool water.”
I didn’t give him a chance to respond, I went to the bathroom and took a much needed hot shower.
Once I was clean, I wrapped myself in a towel and walked towards the door to the bedroom. As soon as I opened it, I got scared, because he was sitting there on the bed waiting for me, still naked.
“Oh! Shit! You scared me!”
“Don’t grab anything, go out to the living room right now.”
His tone sounded so serious. “Ok… did I do something?”
“Go…to the living room, right now.”
I walked out, really afraid I’d said something, or done something, or worse, if he went through my phone and saw some of my posts or something. As I walked, he walked behind me, until he basically walked me over to the sofa. At that point, I turned around and faced him.
“What’s going on?”
He reached forward and undid my towel, revealing my naked body. I started to think… maybe I wasn’t in trouble?? But then he pushed me on to the sofa. I didn’t say a word. He used his legs to push my legs open and stood between them, then got down on his knees between my legs.
…OH!! I’m not in trouble! He grabbed my legs behind my knees and pulled me towards him a bit, before he pushed my knees towards my body, bending me in half, my knees by my shoulders, my back on the seat of the sofa, my pussy facing upwards.
I don’t know what it was, but I was super nervous about what was going to happen and it made no sense to me.. he’d already eaten me out before, why was this so different.
As I fought with my nerves, he didn’t say a word, he lowered his head VERY quickly and locked his mouth on my pussy, darting his tongue in to me.
I moaned….LOUDLY, as I felt his tongue exploring my pussy, searching for my clit. As his tongue got closer and closer, my body was tensing up, almost anticipating the feel of his warm tongue on my waiting clit. And then suddenly…. He found it, and the second his tongue made contact with it, he let go of my left leg with his right hand and he darted a finger on his now free hand inside me.
The sudden pleasure of his finger digging in to me and his tongue finding my clit, my body bucked and my breathing became very choppy and he found a rhythm his finger in and out, in and out, and his tongue running little circles on my clit.
“Fuck! That’s so good!” My hips bucked, humping his face.
As he felt more and more tension building he curled his finger inside me and rubbed the upper part of the inside of my pussy. GAAAAAWD!!!! The pleasure I get from that. Now his normal in and out was pair was the bending and straightening of his finger in an undulating motion, driving me WILD. I knew I was getting close to a climax..
Then, he locked his upper lip on the top of and pressed the tip of his tongue against my clit. And he sucked… but as he sucked, he pushed his tongue forward and it ran my clit against his tongue lengthwise. And he did that over and over and over and over.
My hips bucked harder, trying to get space from him to give me some reprieve from the over stimulation, but he had no mercy and kept doing it while still undulating his finger inside me. I put my free leg on his shoulder and tried to push him away, but he just held on harder with his hand that was still on my leg and I couldn’t move him.
“Fuck! Wait, stop, it’s too much!” I tried like crazy to get him to stop, but every attempt on my part just made him go harder. Suck on my clit faster, quicken his finger, and the pleasure just kept building and building. I could feel it in my core.
My breathing quickened again, my hips bucked harder and harder and it became too much. I came. The whole wave hit me, I inhaled and I felt every muscle in my pussy tense up and start to spasm and the moan the left my lips came from the depths of my soul. Wave after wave of warm intense pleasure washed over me. My legs started to tremble and I tensed becoming almost stiff as a board as every muscle in my body from my ankles to my chest all fired for what felt like an eternity, until my body melted and now it was my turn to slump in to the sofa.
I opened my eyes again after almost blacking out and I saw his face with the biggest smile on his face, his beard slick and shiny with my juices.
“Well… looks like you enjoyed that, huh..” he stood up and I saw his dick, hard again, standing at attention. He looked down at it, grabbed it and then looked at me. “How about you help me out again..”
Then… something came over me. I stood up and guided him to the sofa and he sat of his own volition, my guess is he took it as a “yes” that I would get him off again.
As he relaxed, waiting for me to start pleasing him again, but I put a knee on one side of him and was getting ready to straddle him, when HE panicked.
“WAIT!” He grabbed my hips to stop me. “What are you doing? Your [redacted] has one rule and you’re about to break it. We can’t do that.”
I looked at him and now it was my time to smirk. “Don’t tell me you’re afraid…”
The look on his face… a mixture of annoyance, but also… pride! Haha he looked almost proud that I used his game against him.
“Elizabeth… I’m not afraid of shit.” He let go of my hips and he sat back. “That being said, YOU’RE gonna tell her and explain how you got me drunk and took advantage of me.”
I laughed, but then I reached down, grabbed his dick and pushed it against him, pointed at his stomach and sat down on it. It wasn’t inside me, but I was on it.
Then it dawned on me… his dick is touching my pussy…. This is skin to skin… I looked at him and it looked like it dawned on him too. His eyes were big staring back in to mine. Then, it’s like instinct took over and I started rocking my hips back and forth, rubbing my pussy up and down his dick, coating it.
He threw his head back and moaned as I kept grinding on him.
“Fuck mijita…you’re really flirting with the line, huh?”
I stopped grinding on him. “I can get off, right now and just go to bed.”
“NO!” He grabbed my hips and held me on top of him. “No! It’s ok. We’re not having sex, right? This is fine! Keep rubbing on it please.”
“‘Keep rubbing on it.’ Tell me exactly what you want.”
He looked me dead in my eyes. “I want you to keep grinding your pussy on my dick.”
I smiled and went back to grinding back and forth on him. His hands moved from my hips to my ass, and he squeezed and spanked my ass as we mimed having sex, I would call it dry humping, but I was so wet, it was ridiculous.
I leaned back and put my hands on his knees to anchor myself better and used this better angle to ‘dry’ hump on him. His dick twitched frequently, and it was so crazy to me to feel the head of his dick continuously rub up against my clit, giving me sudden jolts of pleasure.
As I kept grinding, he sat up, further pressing his dick against me and he leaned his head down and I felt his mouth latch on to my tit. I moaned and took my left hand off his knee, and grabbed his head, rubbing the back of his head as he suckled on my tit. I had really sensitive nipples… I LOVE when my nipples are teased, pinched, lightly twisted, bit, sucked, name it!
Things were so intense for me, the feel of his body under mine, his dick pushing against my pussy, skin to skin, his hands groping and spanking my ass, his teeth on my breast and his tongue teasing my nipple. I felt my orgasm building again. But I also felt him tensing up too and it felt like a race to see who could cum first.
I picked up speed, bucked harder and faster, pressing my pussy against his dick harder and grinding at a quicker clip, and suddenly he let go of my tit and sat back quickly.
“I’m cumming!”
As he said that, I hit my climax too, and my hips bucked forward, getting his dick off my clit and I felt his warm cum coat the outside of my pussy and I slid back up and back down rubbing his cum all over my pussy and his dick. Then the waves started and I hugged on to him as I came HARD, wetting his dick some more.
We sat there breathing hard, our bodies pressed against each other. Neither of us saying a word, just living in the feeling for what felt like hours, until he finally broke the silence.
“Fuck… Ok…We need to get up.” He tapped my ass. “We need to clean ourselves up, cuz I’m sure it smells like drunk sex in here.”
“We didn’t have sex.” I still didn’t have the strength to get up.
“Yeah, I know.” He used his armed to get me off of him and he laid me down on the sofa. “Let me go get a couple of towels.”
As he went to the bathroom, I laid there. Tired, thirsty, and starting to succumb to exhaustion. I closed my eyes just as a towel landed on my chest.
“Come on mija, clean up and let’s get to bed. I have to wake up early tomorrow, and I’m pretty sure you’ve earned another reward tomorrow.”
I grabbed the towel and started cleaning his cum off my pussy.
“Would this be a weird time to ask for more money for tomorrow?”
He laughed. “Do you want me to put it on your bedside table, so when you wake up, you have the whole prostitute experience?”
I laughed, and then he came over and helped me up and we walked to bed, where we laid down, spooned and passed out.
I was not prepared for everything that happened.. and we still had 2 more days together…