I woke up to Cindy working on deep throating my cock. Her gagging, and coughing was what woke me up from a sex dream. I looked down to see her forcing her own head down onto my thick pole. She had made some headway though. She used to only be able to suck a little less than half of my cock, and had room enough for both of her hands by the base. Now she could get almost two thirds of it into her mouth, and only had enough room for one of her hands.
I pulled her legs up over my face, and returned the favor. Her humming as I ate her out added a little something to the blowjob that she was giving me. I held onto her ass cheeks with my hands, pressing her sweet pussy onto my mouth. I didn't relent on her clit until I made her cum all over my face. Then lapped up her juices as she sucked my cock. Seeing, and feeling her body jerk every time that she gagged herself, and hearing it, brought my nut on faster. It wasn't long until I was cumming in her mouth.
We laid like that, licking and cleaning up each other's messes for a while. Then got up, and cleaned each other in the shower.
We made breakfast with each other, and talked about nothing at all that was important. Just general comments about the weather, and current events that was happening. I could tell that she was fighting with herself not to pester me about her surprise. She slipped a couple of times.
We kissed goodbye, and she left for the day. Katherine's plane was taking off at noon, and she would arrive in Portland a little after three. She told me that she'd hang out at the airport until I could get there to pick her up. I felt bad about that, and offered to leave early to pick her up, but she insisted that I didn't.
Today was the day that we were all going to Old Orchard Beach. OOB wasn't far from Funtown, but because of the drive down the strip, and finding parking, I left early. Everything was picking up by the time that I got there, but it was easy enough for me to find a place to park.
I pulled up the Facebook page, and looked to see where everybody was meeting up, but it did not specify. I guess that it was a free for all. I got a text from Kim asking me where I was at. I replied that I was at the Oceanside Grill. It was a place that, like the name said, was on the beach. She texted back that her, Heather, Suzie, and Rachel were all riding in together because of the parking, and that they would catch up with me as soon as they found a place to park.
They got there about half an hour later. I greeted them with a hug, and a kiss each. I already had a table for us out on the patio near the beach. It wasn't even 10 yet, so I was drinking coffee. They ordered coffee too, and we sat there talking.
“Has Candice called, or texted you yet?” Kim asked.
“No, honestly, I didn't even think to give her my number.” I said.
“I'll text her.” Kim offered, and plugged away at her phone.
“So, we all have your number, and she doesn't. Aren't we special.” Heather laughed, and winked at me.
I just smiled, and winked back.
“Ok, Matt just dropped her off at the pier, and she's heading this way.” Kim told us. “I guess that he, and his goons are all heading to a place called Pirates Patio.”
Suzie did a quick map search on her phone.
“That's clear on the other side of the beach.” She said. “I guess that they don't really want to catch up with the rest of us. It way off the beaten path.”
“Oh well, they would probably do nothing but drink, and I remember how handsy they all were when they were drinking back in school.” Rachel said. “I was creeped out then, and really don't want to deal with that for a whole week.”
“Hell no.” Heather agreed, laughing.
Candice arrived shortly after. The girls all greeted her with a hug. She gave me a hug hello as well, and added a kiss like all the rest of the girls had. It took me by surprise for a moment, but rolled with it. I caught Kim grinning at me out of the corner of my eye as I sat down.
“So, what are we doing today?” Kim asked. “Truthfully, I'm not a huge fan of the ocean. The salt always gets in my mouth.”
“I thought that you liked salty stuff in your mouth.” Heather joked, causing us all to laugh.
“I can't help it if I love sucking dick.” Kim shrugged, causing all of us to laugh even harder.
We took a moment to calm down. Then looked at each other.
“We could go shopping on the strip.” Rachel offered.
“No, the prices are too expensive here.” Suzie said. “Plus, we're probably going to be doing that tomorrow in Freeport. I'd rather spend my money at Beans, than here. At least they have a lifetime guarantee.”
“Well, it doesn't seem like anybody really gives a fuck if we're here, or not.” Heather said. “Everybody seems to be staying in their own little groups. Why not just get the hell out of here. We can go find a lake, or something.”
“We're going to be at the lake on Friday, but lake days are better than beach days, always.” Candice said. “Where are we going to go though. I'd offer my place, but my kids are there. My oldest is watching them.”
I tensed up for a moment when she brought up Cindy.
“Same here.” Heather, and Rachel said.
“Well, I'm renting the house out on the point.” I offered.
“My daughter loves that house. You don't mind all of us coming over?” Candice asked.
“No, we can pick-up something to throw on the grill, there's a boat, and we can pick-up some booze.” I said.
“Sounds like a plan.” Heather said. “You've been paying for everything all week, Luke. Kim, and I will pick up the tab on this one.”
“I'm going to text Matt, let him know not to get too drunk. So he can drive himself home.” Candice told us.
“Luke, you're going to have to give Candice a ride. My car is full, once we hit the grocery store.” Heather told me.
“That's fine. She can help me get ready while you all are shopping." I said, looking over at Candice.
She nodded, and we all headed out. My car was right there, so we were off in a matter of minutes. Candice was checking everything out in the car. I imagine that it was her first time in one. I did own one years ago, but got rid of it for a better car.
“I can't believe that they rented this thing to you.” She said, smiling.
“A little bit of an upgrade charge, but not too bad.” I told her.
I punched it after paying the toll to get onto the turnpike. It pushed her back into her seat, and she screamed in excitement. We went from 0 to 70 in less that 4 seconds.
“Oh my God, you're going to kill us.” She giggled, as I leveled off at 70.
“Nah, this thing's easy to drive.” I said, looking over at her, and smiling.
Candice got a text, and looked at her phone. She read it, and groaned.
“Matt's pissed that he has to drive himself home.” She told me.
“Doesn't he work for his dad at the dealership, or own it by now?” I asked, playing dumb, and causing her to flinch. “Why doesn't he just call an Uber to get home if he gets that drunk?”
“His dad lost the dealership.” She admitted. “Matt works for a construction company.”
“Oh! That sucks.” I said, but was smiling inside. “Do you need for me to take you back?”
“No, he can calm his drinking for one day.” She said looking embarrassed.
We got to the house. I had to hide a pair of Cindy's panties in my pocket as I gave Candice a tour of the house. Then she went into the bathroom to change into her bikini.
She came out a short time later, still adjusting her tits into her top.
“Having problems?” I chuckled.
She squinted her eyes, and placed her hands on her hips as she looked at me.
“These things are getting out of control.” She said, pointing to her tit as she said it, then put her hands on her hip. “I have to mix, and match my bathing suits every year, because of these things.”
They were pretty big. Back in high school, she was a solid B cup, but now, I'd estimate a large C, maybe a D.
“You have filled out a bit since high school." I said.
“What's that supposed to mean?” She scoffed. “Are you telling me that I'm fat?”
She was trying to hold back her laugh, and look angry as she marched up on me. The she playfully hit me in the shoulder. I was too busy laughing at her mad face to reply, and she kept hitting me playfully. So I did the only thing that I could, and put my arms up to block my head.
She broke down, and started laughing with me. She was still hitting me, so I slipped around her, and wrapped my arms around her, pinning her arms to her sides. She squirmed as I held her, her tits jigging dangerously close to falling out of her top, and her ass grinding on my crotch. My cock swelled rapidly, filling in the crack of her ass.
Her struggling slowed. She must have felt my dick nestled between her ass cheeks, because I felt her flex them a few time as she leaned back against me, slowly massaging my cock. She let out a quiet moan that I barely heard, but I did.
I loosened my grip around her, placing my hands on her sides. As she continued to rub my dick with her ass, my hands began to roam until they were cupping her tits. She let out a louder moan as I felt her hard nipples poking into the palms of my hands.
I couldn't help but lean down an kiss her neck. She gasped, and reached up, grabbing my hair, and holding my head into neck. I began grinding back into her ass as I massaged her tits, pulling her top up to free them from their confines.
“Yes!” She breathed.
I let go of my hold on her tits for a moment to pull both of our bottoms down. My hands went straight back up to her tits as soon as our bottoms were around our ankles. She went back to grinding her ass on me after we had stepped out of them.
“Oh!” She gasped, feeling my full length, and girth with her bare ass.
I nibbled on the back of her neck, sending a shiver down her back. She leaned over the counter, signaling for me to enter her. I reached down, and slid myself in. She was tight, but wet. So I slipped right in.
“Oh God!” She moaned.
I knew that the other girls were going to be showing up soon. So there was no waiting. I started slamming into her straight out of the gate, while she grunted with each thrust.
“I'm cumming!” She screamed, surprising me at how quickly she reached her peek.
I felt her spray on my balls, and legs. Her enjoyment brought me back to why I was there. How she made me feel all those years ago. How she broke my heart. There was no way that I was going to let her off that easily.
I pulled out, and slipped my cock right up her ass. Her cum lubed my dick, and I went balls deep in one thrust.
“Ahh, huh, huh, huh, oww!” She screamed.
I reached around, and pulled her up by her tits as I was hammering into her ass. She grunted, and groaned. I though that I heard her sob, and sniffle as I continued to fuck her ass.
I slammed into her one last time, and came. I held her to me, as I pumped my cum deep into her bum. We were both shaking as we stood there with my cock up her ass.
“Oh my god.” She said breathing hard. “That was a first.”
“Sorry about that.” I lied. “I got a little excited. Are you alright?”
“Yeah. It was probably better that it was a surprise. If I'd known about it beforehand, it probably would have hurt more.” She said. “You caught me in a very relaxed state, so it wasn't that bad.”
I felt her asshole tighten around the base of my cock, and realized that I was still in her ass. She groaned, and then giggled.
“It wasn't that bad, for my first time.” She said. “After the initial shock of it wore off.”
“Well, I'm glad that I could be your first.” I chuckled. “The other girls are going to be here soon. We don't have time for a shower, and we need to air this place out. I say that we keep the back door open, and run down to the lake to clean off.”
“That's a good idea, but it's going to be a little hard for either of us to run with that beast still in my ass.” She laughed.
I laughed with her, and pulled my cock out. She hustled out the door, while I gathered out suits, and followed. She looked to be moving a little gingerly, and I smiled as I watched my cum running out from her ass, and down her thighs. The inside of her thighs were coated with her cum.
We dove into the lake, and surfaced. We stood where the water was at her chest level. It was easy enough for me to clean off. A couple of swipes with my hand, and I was done. She took a little longer, and me watching her got her embarrassed. Her face was getting a little red.
“I was a little afraid that it wasn't going to close back up.” She said as I handed her bikini bottoms. “It took a little longer than I thought.”
She got dressed in the lake, and the girls arrived shortly afterwards. We got out, and went back up to the back deck. They got burgers to cook, and a few different liquors, and mixers.
Suzie got to work on making Margaritas for all of the girls. I stuck with my Jack and Cokes, and fired up the grill. Heather, and I kept our drinking light, while the rest of the girls hit it hard. By mid afternoon, they were flashing everyone else, and getting rowdy. Heather and I were laughing our asses off when the 4 of them stripped off their bikinis, and ran to the lake to skinny dip. They each fell no less than 3 times getting down there.
We wrapped up the party around 5 that night. Heather said that she'd make sure that everybody got home ok. It was just as funny watching all of them getting dressed in the living room. None of them seemed to mind that I was there, and was seeing everything that they had.
After they left, I checked my phone. Katherine had sent me a text, telling me that she landed. It was sent an hour earlier. I texted her, and told her that I was on my way. Then sent a text to Cindy, telling her that I had to run an errand, and that I would text her when I got home.
I hopped into the car, and raced to the airport. Katherine was waiting for me outside of the Arrival Terminal. I pulled up in front of her, and hopped out.
“I'm sorry, Babe. The party lasted longer than I'd hoped.” I told her, walking around the car, and giving her the most passionate kiss that I could.
She smiled at me after the kiss. “You have nothing to apologize for. I knew that you were going to be running late. But, that kiss was definitely nice.”
I smiled, and took her bag for her, packing it in the car. Then opened the door for her. I hopped into the driver’s seat, and headed out.
She took my hand in hers, and told me to fill her in on everything. She knew about most of it, but I filled her in on my week so far. She started laughing at the end, when I told her about earlier.
“You cheeky bastard!” She laughed. “You buggered your ex, and her daughter. You fucked one of her friends, and by the sounds of it, you could get any one of the rest of those tarts. Somebody has been a busy boy.”
“I'm just worried about Cindy. By the sounds of it, she had a rough life already. I really don't want to pile on.” I told her, squeezing her hand gently.
“Well, she sounds like she's tougher than you think. She already knows that you are only here for the week, and entered into a sexual relationship with you anyway.” Katherine reassured me. “You just leave the rest up to me.”
I let it go, and drove us back to the lake house. I showed Katherine around the house, and the back yard. She really seemed to like it.
She had me text Cindy while she went upstairs to unpack. Cindy replied that she was on her way. I waited for her to arrive, and actually was nervous. Half an hour later, her car pulled up. She gave me a kiss at the front door, and followed me out to the back deck. I lit up a cigarette, and sat in a chair. Cindy took the seat next to me.
“So Daddy, have I been a good girl?” She asked, acting cute.
“Yes Daddy, has Cindy here been a good girl?” Katherine asked from the doorway behind Cindy.
Cindy was startled by Katherine. She jumped, and turned to see who it was. Her jaw dropped when she recognized Katherine.
“Oh my God! You're Katherine Wales!” Cindy screeched.
“That I am, Dear.” Katherine answered, walking out to us. She gave me a kiss before turning back to Cindy. “And, you must be Cindy. I've heard so much about you.”
“Ah.” Was all that Cindy could get out. She looked scared.
“Luke honey, why don't you go get all of us some of those Italian Sandwiches that you've told me so much about, and give Cindy, and I some time to talk.” Katherine recommended.
I nodded, and got up. Katherine gave me a kiss, and took my seat. Cindy looked like she didn't know what to do. I leaned down, and gave her a kiss before taking off.
Amato's was packed, and it took me half an hour just to place my order. It took another 15 to get it. I was gone for just over an hour. I walked in to Katherine, and Cindy laughing, and having drinks together.
“Hi Daddy!” Cindy squealed. She got up out of her chair, and leaped up on me, giving me a passionate kiss. “What took you so long?”
“Amato's was packed.” I answered, as she slid down off of me.
Katherine got up, and gave me a kiss as well, and took the bag of sandwiches from me.
“Go mix yourself a drink.” She said.
I did just that, and joined them for dinner.
“Katherine explained to me what's going on.” Cindy told me. “I can't believe that my parents did that to you, but I wouldn't put it past my dad."
“Well, he's the one that told me about it all.” I told her.
“Cindy is on our side. She doesn't like her current situation.” Katherine told me. “So, she's going to be coming with me up to Montreal for the rest of the summer. Then she's going to transfer out to UCLA to start school there in the Fall. She wants to become an actress, we figured that seeing me work, and how things are done, will help. Plus UCLA has a better Drama Department than USM.”
“Is that what you really want to do?” I asked Cindy.
“I'll still take Business Management Courses, in case acting doesn't work out. I've already told you about my home life.” Cindy said. “Katherine said that I could live with the two of you while I'm out there.”
I agreed to it, and told Cindy not to worry about student loans. I told her that I would invest in her acting career, and pay for her schooling. She got really excited about it, and gave me a kiss.
We all stayed up drinking, and talking about the next few days. Katherine told me that she really liked it there, and that we should at least stay the weekend. I called the owner of the house, and asked him to extend my rental until Monday morning. He agreed, telling me that it wasn't booked. I told him to just run the same card for the difference.
Sleeping got a little cramped. Katherine didn't want to kick Cindy out of the bed just because she was now there. Cindy offered to take the other bedroom, but Katherine insisted that she stayed with us. I got stuck in the middle, with them sandwiching me in.