Cruising Ch. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Ronnie said that you paid for her and Bob's trip. You did that too?" She asked.

"I don't think that's any of your business." I said flatly.

Debbie turned to face me. "I'm not prying, I'm just curious."

"No, you are prying. Would you like a drink?" I asked.

"Yeah! Do you have any vodka?" she asked.

"Yes. How do you like it?"

"With orange or pineapple juice. Do you have any?" she asked hopefully.

"Afraid not. How about a lime? Do you want ice?" I asked.

"Yes please, a lime and ice." Debbie said.

She wandered over to the windows and looked out. "A balcony! Can I go out there?"

I shrugged, "Suit yourself."

Debbie opened the door and stepped outside to the railing. She put her handbag down on a lounge chair, leaned over the rail, faced forward and raised her arms up. The scene reminded me of a dog sticking his head out of a moving car's window. She seemed to be enjoying the wind in her face. After pouring vodka from my mouthwash bottle I brought our drinks outside.

"Thank you, this deck is amazing!" Debbie said after taking her drink.

"Glad you like it. I haven't spent too much time out here yet except when we departed." I replied.

"Oh shit, I just got an idea." Debbie said wide eyed.

She put down the drink and leaned over the railing as far as she could. She looked forward, then down, then to the stern and finally upwards for unusually long periods of time. Then she looked around on the balcony and at the overhead light.

"Can you turn that light off?" she asked.

"I don't know." I said.

I began looking on the outside for a light switch before moving to the inside. Over by the couch I spied two wall switches that I hadn't tried. One did work the balcony lights.

"Please turn them off. I'll tell you what I want to do later." Debbie said.

We gathered our things and sat near each other on the couch with our drinks and chatted.

"So, how do you and Marsha know each other?" I asked.

"Oh, we met in college. We became friendly and things just progressed from there." Debbie said.

"Where are you two from?"

"I'm from Ohio, Marshy's from Indiana. Did she mention that we play together? We like to do three or more somes." Debbie said casually.

"Yes, she did mention that." I replied.

"Not that I'm not enjoying our conversation but do you think we can get going? At midnight there is a chocolate buffet up at the sky pool that I hear is to die for." She said.

"Oh, of course. I was really enjoying your company but I understand." I said.

Inane small talk bores me to tears so I had no issue with getting down to business. Debbie stood and kicked off her heels. She turned around and backed up to me.

"Would you mind getting the zipper please." She asked.

I stood and pulled down the zipper of her dress. It went all the way down to the center of her well filled ass. The dress looked like a Hawaiian dress with dark blue flowers all over it and it was cut just right to accent Debbie's assets and hide her flaws. She shook her way out of the dress and laid it on the couch. I soaked in the whole view from behind. I'd never seen a six hook bra before tonight. It was definitely designed to hold some serious weight. She is pear shaped, meaning from the waist down things get thick. Very thick. She was wearing black lacy panties that rode below her waist be ended half way down her big ass with just a thin piece going under and around to the front. Her hips were very wide and thick. Her thighs were massive with heavy saddlebags. From her knees down she was average but from the knees up to her waist she was supersized. She looked even better when she bent over to lay her dress down on the couch.

She turned to face me and asked, "Are you disappointed?"

I moved closer and pressed my crotch to her thigh so she could feel my erection. "What do you think?"

She's several inches shorter than I am but reached up to hold my face and bring it down to her level to give me a long kiss. "I like that answer."

Debbie reached behind to undo her bra and I stopped her. "Wait, I want to do that."

I scored more points.

"You can but first I need you naked." Debbie grinned.

Debbie began unbuttoning my shirt. I helped by unbuckling my pants and kicking off my shoes. Quickly she had me nude except for my socks. I sat down and those were gone too. My prick was standing up and rock solid.

"I really want to give you some head now and I really want you to undress me. We can't do both at the same time so you decide what happens first." Debbie said actually trembling with anticipation.

I really wanted to unleash her tits. In her black bra they were massive. Each one was about the size of a honey dew melon. Instead on the bullshit padded shelf bras (that's what I call them and I hate them) the cup material was thin and supportive. The material was stretchy like lycra but thin and shear like lace. I could see the pale pink outline of her areolas through the material and her nips were definitely stretching the material further.

I moved behind her taking my time not wanting to rush this phase at all. I placed my hands on either hip and began squeezing and feeling her girth. My hands were still on her panties and not touching skin yet. I worked my way up to her midriff finally making skin contact causing her to shudder a bit. I moved to her forearms and rubbed my hands slowly up to her shoulders. Now it was time for my fun. I stepped in closer and pressed my prick into the crack of her ass. She reached behind and pulled me closer making an 'mmmmm...' sound. I lowered my hands down the front placing my finger tips of each hand at the top of her cleavage. Slowly I moved my hands down moving from exposed skin to the brazier cups. Once I got to the lower third I stopped and lifted them to feel their weight. Debbie was practically melting against me. I moved my thumbs and located each nipple and moved around them but not touching them directly. I slowly began humping my cock into the crack of her ass.

"I am so close to cumming it's making me crazy." Debbie said.

I pulled my hands back from her tits and back down to her hips. Hooking my thumbs into the top of her panties I work them downwards slowly in a rocking motion. I couple of inches on one side, a couple on the other until the panties fell to the ground. Now I moved to the back of the bra. It was quite a piece of engineering to be about to support this much mammary meat. I undid one hook at a time until all six were open. I lifted the thick straps up off her shoulders and carefully removed the bra from each boob one at a time. I tossed it on the couch and placed my hands on Debbie's hips again. I knew if I touched her pussy that she would cum.

"Are you a squirter too?" I asked quietly in her ear.

"No. I wish. But I do get real wet. I'm fucking real wet right now and I hope you are going to do something about it really fucking soon." Debbie said in an unsteady voice.

I'm sure that every guy or girl that Debbie has ever been with went straight to her tits without passing go or collecting $200. I wanted to be different. I slowly released her saying, "I'll be right back."

I went to the bathroom and grabbed a fresh towel. Even the wet ones Marsha and I used we replaced with new ones. I went back to the bed and spread out the towel. I got to remember to keep some towels closer to the bed from now on. Debbie was still standing by the couch downing her drink. I took her glass and set it down and then took her hand and led her to the bed. I had her lay down on her back with her legs spread.

"Wait, I promised to suck your dick." She protested.

My response was to place three fingers on her pussy lips and gently massaged her. Immediately Debbie grabbed two handfuls of blanket, arched her back and cried out, "I'm cumming!"

Her body buckled strongly a few times so I waited for the spasms to subside. When she recovered I began moving my fingers again.

"That was astounding! No one's ever made me cum like that before. I mean from just touching my lips. How the hell did you do that?"

My one reply was a smile and more manual stimulations. I wasn't getting anything close to the same reactions since she wasn't as primed up like the first time so I moved down to lick her pussy. We quickly found a rhythm of her humping my face, my licking and sucking and her cumming. She was a fast cummer. Almost as one ended the next one was building up. After about ten minutes of virtually nonstop orgasms she called me off.

"Damn, you are killing me. Marsha was fucking right, you do know how to lick a pussy. I'm too wasted to give you decent head right now but I want you to fuck me from behind. You got to use a condom. All right?" Debbie said.

"No problem." I said standing to get one I pre staged in the night table drawer. I rolled it on as Debbie rolled over onto her belly.

I was raring to go and got on my knees between her legs but she remained flat on the bed.

"Do you want to get up on your knees?" I asked.

"No, I like it like this." Debbie replied.

"Do you want me in your ass?" I asked.

"No, fuck the pussy. Don't worry, you'll reach." She said.

I moved forward and pushed my way between her big ass cheeks and thighs. I had to feel my way around since I couldn't see through all her skin. I did find her hole and pushed the head inside. I already knew she was wet. I soon found out she was very tight. Logically I know that bigger women are no tighter or looser than anybody else it's just when you see a big woman you expect a big pussy. Debbie made adjustments to her position to make access easier. I was hunched over her massive ass working my way inside. Every time I thrust my hips Debbie gave a satisfied grunt. I learned how this was going to work best. I was bent over half lying on her ass and holding my torso up with my hands on either side of her waist. This really was a comfortable position.

I began to slow stroke her pussy. I could see her fingers white knuckle the blanket on every in stroke.

"Come on! I ain't no delicate flower. Give it to me good and hard." Debbie commanded.

I picked up the strength and pace of my thrusts. About once a minute Debbie cried out that she was cumming again. When she came her pussy squeezed my dick even harder. I was enjoying this position with her. Every time I pumped my cock into her I was met with her ass and thigh meat. I felt like I was fucking all of her.

"Come on baby, cum for me. I want to feel you squirt your cream inside me. Fuck my pussy hard until you dump your load in me. Do it for me baby!" Debbie cried out.

I did cum long and hard. All my strength left me when I came and I collapsed on top of Debbie who was crying out with another orgasm with me. When I was spent I had no energy to move and was quite comfortable.

"Damn, you really know how to throw in some serious dick. I can't remember the last time I came so many times during one fucking." Debbie said.

"Believe it or not I enjoyed it too." I replied weakly.

"That was my first onboard fuck. I hope all of them are like that." Debbie said.

We rested for a minute until Debbie broke the silence. "Can I make myself another drink?"

I lifted myself off and out of her saying. "Sure."

I rolled over onto my back and Debbie stood up seemingly full of boundless energy. She poured a drink asking about the mouth wash bottle and complimenting me on my ingenuity. She took her drink and her purse and went out onto the balcony and lit up a cigarette. She sat in a chair smoking and drinking by herself. I got up and washed up in the bathroom before pouring myself a refill and joining her.

"Let me know when you're ready for another round. I have some special plans." Debbie grinned.

"Want to let me in on them?" I asked.

"Not just yet. So tell me, you're not a tit man? You're an ass guy?" Debbie asked.

"I like them all, just so long as they are attached to big woman." I said sitting and enjoying my drink.

"You are the first person I've ever been with that barely touched my girls. Everyone else the first thing they go for is my tits." I was told.

"I figured that so I decided to go another way. From what I've seen they are quite impressive." I replied.

"Yeah, and all real too. I wish they were more sensitive though. Some women can cum from having their tits played with. Not me, they feel good and all but I don't get off from them. Everyone else does though." Debbie said with a giggle.

"I do like your ass too. If felt so nice to bang into it." I said.

"Thanks, up on my knees is nice because I can finger my clit as I get fucked but when I am on my belly getting banged hard makes me cum every time."

"I noticed. So, what are your plans now?" I asked.

"I want to go inside and let you play with my girls. Then I want to suck you good and hard. Then I want you to fuck me in the ass nice and hard." She said.

"OK, what's so special about that?" I said out loud.

"You'll see. Just let me know when you are ready." Debbie smiled.

We moved back inside. Debbie brought me to the couch and we sat side by side. She leaned back presenting her tits to me. They were big and firm. Her areolas were pale pink and faded into her pale white skin. The nipples were on the small side but always seemed to be hard. I worked them over for a few minutes while Debbie lay back moaning. I slid a hand down to her crotch and she spread her legs wider allowing me access to her clit. Her hips began to work against my hand again. Suddenly she sat up.

"Oh no you don't. You keep this up I'll never get to suck your cock." She said playfully.

Pushing me off of her Debbie stood up. She pushed the coffee table to the side and kneeled down on the floor. Gobbling up my semi hard dick in her mouth she began some very uninspiring head. There is more to sucking a dick that just moving your head around. I guess no one ever showed her the tricks. After a few minutes of this she released me and positioned herself to wrap her tits around my cock. Apparently Debbie understood Russian a lot better than French. She had a wicked grin on her face as she tit fucked my prick and was doing it well.

"I've lost count how many times guys have lost their load on my tits like this." She said proudly.

"I can see why, you do it very well." I complimented her.

She chuckled, "Well, it helps to have the right tools. Please tell me you have some lube around."

"I do. So tell me your plans." I said.

"Better than that, I'll show you. Go get the lube." Debbie said releasing my dick.

I stood up and went to the night table draw. It took a minute to remove the protective wrapping off the brand new squirt bottle I'd bought just for the trip. Meanwhile Debbie stood up and moved to the end of the bed.

"OK, I'm going to trust that you are clean. You can ass fuck me without protection." Debbie said.

Still standing she spread her legs apart and bent over the foot of the bed. "Grease up and go in slow at first."

I moved behind her and enjoyed the view. I went down to one knee and tickled her sphincter with my tongue for a few seconds making Debbie laugh. "Marsha likes to do that to me too."

I stood back up and applied lube liberally to my cock and her ass. Tossing the lube bottle on the bed I grabbed her ass hips and eased my way inside. There was almost no resistance, I slid in easily.

"Oh yeah, that's good. Do me hard, I like it like that." She said.

I began working my way in and out but not giving her the full length just yet. It felt really good and I felt her tightening up around me. She let out a long groan of satisfaction.

"All right, that's a good start. Pull out and come with me." Debbie commanded.

I did as asked and Debbie opened the door going out to the balcony. She walked right over to the rail, grabbed it with both hands, lowering her head so her chin was almost resting on it, spread her legs and called back to me, "Now do me hard and don't stop until you fill my ass with your spunk."

I was good with this. Pushing hard I reentered her ass causing her to grunt. I pounded her ass hard feeling the night breeze flowing around us. The thrill of fucking outside was very nice. Continued to fuck her harder and harder. Debbie was encouraging me. Over time I'd pushed her forward so that she was standing almost upright. Still holding the rail now her head and tits were out over the ocean. Her belly and thighs were pressed against the glass wall below the railing. She could move no further forward. I was close enough to hold the railing so I grabbed it for more leverage.

"I'm cumming!" Debbie cried out.

I pounded harder and forced her hands off the railing. Basically from the waist up she was hanging overboard in the wind. It seemed like my dick in her ass was the only thing keeping her onboard. I'd guess Debbie had seen Titanic a couple hundred times. This was her "flying" scene.

She kept cumming calling out regularly and I kept fucking. Reaching around I grabbed the tits flopping around in the wind and squeezed them hard.

"OWW! Not so hard!" Debbie cried out.

I was on the verge when her ass tightened up again and she said, "I'm cumming" for the umpteenth time in the last hour or so. I released my load inside bringing about another cry from Debbie.

"So cum already!" A male voice called out.

Somebody was nearby on their balcony or on an outside deck and shouted out. This was soon followed another cry of, "Come to my room and I'll make you cum too." Then, "Give it to her good buddy!"

Debbie was tired but still had her modesty. She used her strength to push me backwards. She had a look of fear in her face.

"Do you think they saw me? Would they recognize me?" She asked.

How would I know. She had her head out there. All she had to do was look around.

"I doubt it. They didn't sound too close. If they were on either side they might have seen a profile. Anyone above would only see the back of your head." I said rationally.

Unconsciously she crossed her arms and covered her tits. "What about below?"

"You were looking down. Did you see anyone? Think about how hard it is to look up from a deck or window." I said calmly.

Debbie looked frightened. She stepped inside and went right to the bathroom. I closed the balcony door and walked to the closed bathroom door. I knocked softly.

"Are you all right?" I asked.

"Give me a minute." Was all she said.

I went and found my drink. In a few minutes the bathroom door opened.

"You can come in now."

Debbie was at the sinks washing her face. There were some tears and her makeup was ruined.

"Are you OK?" I asked.

"What's done is done. If I'm recognized so what. Could I take a shower so I can wash my ass off?" she asked.

"Of course. I'll join you but I need to take a leak first." I replied.

Debbie suddenly got excited. "No, wait! Don't go yet."

The tub is big. Oversized to allow an average couple to lay in side by side together and enjoy the water jets. Or, it can fit one large woman comfortably. Debbie climbed into the tub and lay down. She bundled her shoulder length brown hair together and held it behind her head with both hands.

"Piss on me, I love it. Just try to not get it in my hair please. In my face is ok." Debbie practically begged.

"You sure?" I asked.

"Fuck yeah, I love it. In college at a frat house I once had 39 brothers taking turns pissing on me all night long. They had a kiddie pool in the middle of the room and a couple kegs of beer. They drank hard and when one had to go he would piss at me. They would have contests who could get the most piss in my mouth. They wouldn't lower themselves to fuck me but pissing on me was fine. I didn't care, I got what I wanted. I fucked half of them anyway but they would never admit it to their brothers." Debbie said.

"All right. Just say stop if you need to." I said.