A Trip Out Boating

"Jason, hurry up!" Chris yelled.

"Hold on, give me two minutes." I yelled back.

"Jason, we are leaving!" Brent yelled.

"Okay, okay. I'm ready." I told them both as I walked out into the parking lot of the hotel.

Our friend, Dan, was getting married, and he flew us all down to Cabo for his bachelor party. Chris was Dan's best man. Brent and I both worked with Chris. We got to tag along on the trip because Chris insisted we were there. We knew Dan a little, but not too much. Dan was crazy wealthy. Springing for two extra people to attend his bachelor party was nothing to him.

"Get in the taxi!" Chris yelled at me.

"I'm here, I'm going. Relax." I told them both as I jumped in the back seat of the taxi.

"How far is this place?" Brent asked Chris.

"I don't know, maybe ten minutes." Chris replied.

"Dan paying for this, right?" I asked.

"Not the boat, no. We can cover it thought. I won't be much." Chris answered.

We arrived at the marina and found a place to rent boats. Unfortunately nothing was available that day.

"Fuck me." Chris said to himself.

"What's up?" asked Brent.

"Check her out." Chris said looking out toward the boats.

"Where?" Brent asked.

"Right there. In the yellow bikini." Chris said pointing out an attractive woman in a yellow skimpy bikini standing on the side of a very nice boat.

"I see. Damn, she is freaking hot!" Brent said.

"Where? Where are you two looking?" I asked them.

"Right there." Brent pointed out near the middle of the marina.

"Chris, what are you doing?" Brent yelled. Chris was walking quickly toward the boat and the woman in the bikini.

"I bet he is going to talk to her. Let's go get him." I told Brent.

"Oh shit. Look, a guy just walked up from down below in the boat." Brent said as we both walked following Chris towards the boat.

"To late, Chris is already talking to them." I told Brent as we both watched Chris step on to the boat.

"I hope he isn't getting us into some sort of trouble." Brent said.

We walked up on the boat and Chris was chatting with the couple. They were laughing, so that was a good sign.

"Hey guys, this is Annette and Jay. We are going boating with them today." Chris said.

We all introduced ourselves. I wasn't sure how Chris worked it, but that was his charm. He always talked his way into anything.

"Hi guys, I'm Annette." Annette said as we got on the boat.

"Nice to meet you. Wow, this is a very nice boat." I told her.

After some small talk we were all on the boat and headed out to sea. It was a beautiful day. Annette and Jay seemed very friendly.

"Is this a boat or a yacht?" Brent whispered to me as we stood near the back of the boat and Chris was getting a tour down below.

"I don't know. It's big, so I'm going with yacht." I whispered back. "Spending the day out on a yacht in Cabo sounds better to me anyways."

"You guys should go down there. It has everything!" Chris yelled at us as he came back up from his tour.

"Yes, we need to check that out." Brent answered back as we both were still adjusting to the fact that we were heading out to the ocean somewhere with a couple we just met.

"Guys, we have a fully stocked bar, please make yourselves at home." Jay said to all of us.

The next few hours went well. Brent and I adjusted to the situation. We had a few beers, and we're enjoying the trip. We both couldn't keep our eyes off Annette, but we were trying. We didn't want to upset Jay, especially that far out on the ocean.

"Dude, I can't stop looking at Annette." Brent whispered to me as we sat in some chairs at the back side of the boat.

"I know, that bikini is revealing. It's like the skimpiest bikini I have ever seen." I told Brent.

"You think they are married?" Brent asked me.

"No, I heard Chris ask. Jay is her boyfriend." I told him.

"Look, look. Are you seeing that?" Brent said I a low voice out the side of his mouth.

"Yes, I'm seeing this." I told Brent.

Annette had been walking back and forth on the back of the boat moving things around and cleaning up some things. In all the moving, her nipple came out of her swimsuit, and she either didn't know or didn't care.

"You should tell her." Brent said to me.

"Why me? Maybe her boyfriend will notice and tell her." I told Brent.

"Where is her boyfriend?" Brent asked me.

"I think he is down below with Chris." I said.

"No, look, they are up top driving the boat." Brent said and pointed up a long tower with a ladder up to an area to drive the boat.

"Man, I didn't even see them walk by. I'm so into this girl I don't even know what is going on." I joked.

"Are you boys doing good on your beers?" Annette asked. She was standing in front of us with one of her breasts half-way out. I tried not to look at her nipple.

"I could use another one." Brent told her.

"I'm okay on mine. Thank you for asking." I told Annette.

"Sure, I want to make sure you two are having a good time. Brent, I'll be right back with another beer." She replied.

Annette brought back a beer for Brent. Her breast was still half out.

"If you two don't need anything else, I'm going to work on my tan." Annette told us.

"I'm good. You work on your tan." I told her.

Annette placed down a large beach towel across from us. She laid facing away from us and face down. I'm assuming this was the direction to get the best sun. It wasn't more than a minute or two and the bikini top came off. She was face down, so it wasn't a big deal.

Brent and I continued small talk about basically nothing as we both watched Annette work on her tan. We looked up and saw Chris and her boyfriend also watching her work on her tan.

"Oh my god." Brent said when Annette reached back and adjusted what was an already tiny back side to her bikini, and made it even smaller. She basically made the back side of her bikini a thong.

"I'm not sure I can take this much longer. It's like she is teasing us." I told Brent.

"I know, her entire ass is showing." Brent said.

"Fuck me!" I said in a much louder voice than I should have. Annette got up on all fours. Her top was off and she arched her back. Brent and I were staring right at her ass which was arched enough that we could all but see her pussy. She played it off like she was stretching but her stretch was the biggest turn on.

"It's hot out here guys." Annette said as she stood up with her top off and facing us. "I need to get me something to drink."

Annette walked by us wearing only a tiny bikini bottom with most of is pulled up her ass and showing off her ass cheeks.

"Jason?" Annette yelled from down below.

"Yes?" I answered back.

"I need your muscles for a minute. Could you come down here?" Annette yelled back up.

"Sure." I said and headed down stairs.

I walked down the steps to see Annette on all fours pulling on a cabinet door that was underneath a seat.

"This door always gets stuck and I'm not strong enough to get it open." Annette said.

I got down on the floor next to her and pulled on the cabinet door. It was hard to open but came open after a hard pull.

"There you go." I told her.

"You are so strong, thank you. Our corkscrew is in here. I'm going to open a bottle of wine. Would you like some?" Annette asked.

Both Annette and I stood up. She was in front of me basically naked. I was fighting back and erection but the erection was winning.

Annette walked behind a bar counter to get some wine glasses.

"Would you mind opening this for me?" Annette asked.

I walked around the counter and Annette handed me the wine bottle and wine opener. At this point, I had a full on erection. I was trying not to let her see, but it was sticking out.

"You like wine?" I asked while opening the bottle.

"Well, hello!" Annette said.

"I'm sorry, hello?" I asked as I was confused at her answer.

"Yes, hello." Annette said again with a smile.

I opened the wine bottle and put it on the counter. "Hello? Is that a type of wine?" I asked still confused.

"No, no. I'm telling you hello silly." She said pointing down at my erection.

My face had to have turned bright red. I was embarrassed.

"I'm sorry." I said and covered it with my hand.

"That's nothing to be sorry about. I'm flattered." Annette said as she stepped closer to me.

"Annette?" Jay yelled from up top.

"Yes." Annette yelled back.

Jay walked down the stairs and I froze. Annette was almost completely nude, and I'm standing there with a massive erection popping out of my swimsuit. I didn't have a clue what to say or do.

"I caught you!" Jay yelled.

All I could think was that I hoped he didn't have a gun. I was ready for him to go off on me.

"Yes you did." Annette said back.

"Annette, I told you not to get my good wine." Jay said smiling and I started to breathe again.

"We have guests. I didn't want to get the other wine." Annette told him.

Jay walked into a different room but still close to us. He was looking for something.

"I want to show Chris the new GPS I bought. Have you seen it?" Jay asked from the other room.

"I have not honey." Annette answered.

I was nervous about my erection and didn't want jay to notice, so I stepped behind Annette so that when he came back out he wouldn't see.

"What are you doing?" Annette whispered as I got behind here.

"I don't want your boyfriend to see this" I whispered back.

"I see, gotcha. I'll help." Annette said.

Annette backed up on me. Her ass went right into my erection. I stepped back, but she kept coming. For every step back I took, she took one too until I had my back to the wall, and she had her back to me. She was pushing back hard on my cock which only made my erection harder.

"What are you doing?" I asked her.

"I'm hiding your boner." Annette whispered back while smiling.

"Really? Like this? This is obvious." I told her in a low whisper.

"I have an idea, step in closer to the counter. It will cover you." Annette said as we both stepped in close to the counter which came somewhere between my chest and my waist.

We stood side by side an Annette's hand come right down and grabbed my hard cock.

"I found it." Jay said as he walked back in the room.

"You lose everything" Annette said. "You lose more things than anyone I have ever seen."

"You are not one to talk Annette. You are almost as bad as me." Jay said.

Annette was smiling and talking, the entire time she was holding my cock in her hand.

"Wait, is it working?" Jay asked himself as he looked down at his GPS.

I motioned to Annette while Jay was looking down that she was holding my cock and needed to let go. Without speaking, Annette responded by mouthed the words "I'm hiding it!"

"Honey, is it not working?" Annette she's as she moved in front of me to get closer to Jay,

"I don't know." Jay said completely preoccupied with the device.

"I'm sure you can fix it." Annette said as she let go of my cock, which she had a hold of outside of my swimsuit, only to immediately reach her had down into my swimsuit and grab it with her hand.

"I'm just not sure what's wrong?" Jay asked still not paying any attention to us.

Annette, standing mostly in front of me, managed to work my cock out from my swimsuit and aimed it at her ass. She was trying to push my cock inside her. With one hand behind her back, she stood on her toes and tried to get her ass as high as she could. With her other hand she reached back and pulled her bikini to one side.

Nervous, I tried to back up. Annette had a firm grip on my cock, and she was not letting go. I was scared Jay would look up at us. I couldn't think up a way out of the situation. I decided to go along with Annette rather than making a scene and calling attention to what was going on. I stepped forward and put one hand on her waist. She guided my cock between her legs. My cock pushed up to the outside of her pussy but it did not enter her.

"Almost there!" Annette said.

"I'll figure it out." Jay said without looking up and assuming Annette was talking to him.

Annette moved up and then back down in one quick motion. On the way back down, my cock entered her.

"There it is." Annette said.

"Not yet." Jay said still not looking up.

"Just keep working it." Annette said looking over her back shoulder at me.

I couldn't believe I was going along with this, but Annette felt great. I was so turned on I wasn't even thinking about Jay looking up and catching us anymore. I just started fucking her from behind. Annette leaned forward on the counter to give me a better angle. Her bikini bottoms kept closing in and getting in the way without her holding them to the side.

"Just take them off." Annette said.

Jay was so into trying to get his new GPS device working he didn't even answer. I stopped fucking Annette for a brief second to pull down her bikini bottoms. She stepped out of them and kicked them across the room. They ended up going behind the refrigerator. I was too turned on to care. Annette leaned back over the counter and I grabbed her by the waist and started fucking her again.

I saw someone walking down the stairs out of the corner of my eye. I didn't want to slow down. I was about to cum.

"What are you two doing?" Chris asked as he walked down the stairs. He was looking right at us.

"Getting wine!" I quickly answered as I pulled out of Annette and stepped back. I was on the verge. I was right there, but I knew Chris coming down the stairs would cause Jay to look up.

"Really?" Chris asked as he looked over at us. He saw what we were doing.

"Would you like a glass?" I asked Chris as I pulled up my pants.

"No, I'm good." Chris answered and noticed Annette was walking around without her bikini bottoms.

I grabbed a towel that was on the counter and handed it to Annette.

"What are you working on?" Chris asked Jay as he put his arm around his shoulder to get a better look at Jay was doing. Chris also blocked Jay's view of seeing Annette and I.

"Got it. It's working now." Jay proudly started and looked up.

I was holding a glass of wine. Annette was standing behind the counter with a small white towel wrapped around her waist. At first glance, it seemed like just on an ordinary small towel. But after looking for a moment, the towel was made of a very thin material, and it just barely was able to be tied at Annette's waist.

We all walked back up to the outside and went to the back of the boat.

"You so owe me for this!" Chris whispered to me.

"That wasn't me. She initiated all of that." I whispered back.

"Sure, whatever." Chris replied sarcastically.

"No. I'm being serious, this is all her." I told him.

"Well, I'll do what I can to help." Chris said.

"Help?" I asked.

"Yes, help. By distracting Jay!" Chris said.

"It's not that big of a boat!" I told him.

"Don't worry, I got you. And remember, you owe me one for being a team player on this." Chris said.

"What was going on down there?" Brent said as I sat down next to him.

Annette was walking around looking for something, and Chris asked Jay to take him back up top to show him how his GPS device worked.

"I don't know. I'm still trying to process everything." I told him.

"Why does Annette have a towel around her waist?" Brent asked.

"All you need to know at this point is that she doesn't have anything on underneath it." I told him.

"No?" Brent said with his eyes open wide in disbelief.

"Yep." I said sitting back on the seat.

Annette sat back down across from us. I couldn't take my eyes off her. She had her legs crossed, a towel on her waist that was acting as a skirt, and was topless.

"So what brings you to Cabo again?" Annette asked.

"Bachelor party!" Brent replied.

"Bachelor party? Who is getting married?" Annette asked.

"Jason is!" Brent quickly said.

"No, I am not." I told Annette.

"I'm joking, our friend Dan is getting married." Brent said.

"Dan is one of Chris's good friends." I told Annette.

"Okay, I see." Annette said.

"Jason and I actually don't even know Dan that well. We just wanted to go to the bachelor party." Brent joked.

"This will be my first bachelor party, so I am a little excited." I told Annette.

"First one? Really?" Annette asked.

"Yes, really. I'm actually surprised myself. I guess I have a lot of single friends." I told her.

"Are you excited about it? Do you have a stripper?" Annette asked.

"I think we have two." Brent said.

"Well, you boys will be having fun that night." Annette said.

"It will be a fun night." Brent replied.

"That's something on my bucket list." Annette told us.

"What's that? Going to a bachelor party?" I asked.

"No, stripping for a group of guys." Annette said.

"You can always come to the bachelor party if you want to." Brent said.

"That would be fun, but I better not. That would be a good opportunity to check that one off the bucket list though." Annette paused for a moment thinking. "I guess it wouldn't have to be a large group of men. I think I could be okay with a smaller group, maybe even two men. It's almost the same as a group."

"I agree, two is almost the same as a group. Maybe it's a good way to work up to a group." I suggested.

"There are two of you here right now." Annette suggested with a naughty look. I couldn't tell if she was teasing or serious.

"You should do this now!" Brent said.

"I'm not wearing much to strip out of. Would that be okay?" Annette asked looking for our approval.

"Works for me!" Brent replied quickly.

"I think I have some stripper heels down below. I can put them on to make it more realistic." Annette told us.

"I think adding some stripper heels would be a good touch." I told her.

"Giving a lap dance just isn't the same if the stripper isn't wearing stripper heels." Annette told us. "Let me see if I can find mine."

Annette walked over to a side panel on the boat and turned the radio up louder, so we could really hear the music. She then walked down the stairs.

"Dude, can you believe she is going to strip for us?" Brent asked me.

"I can, yes." I told him as my mind wondered where all this might lead.

"What about her boyfriend?" Brent asked.

"I have no idea. Chris said he would distract him, but that's a big ask for Chris to distract him through a striptease. I don't know how this is going to happen, but Annette is hot, so I'm going along with it." I told Brent.

Annette walked up the stairs wearing a pair of black five inch heels.

"They aren't the clear type stripper heels, but I'm hoping these will work. They are the only five inch heels I could find." Annette said as she walked over in front of us.

"They look perfect!" I told her.

"I guess this little towel is all I have to strip." Annette said to Brent as she stepped over in front of him and danced to the music.

Annette danced a few feet from the seat where Brent was sitting. Brent and I were sitting on a bench type seat with a cushion. It was long and could seat about four people. There was a little space between Brent and I. Annette had a very tone, fit body. The heels she put on really emphasized her sexy legs.

"Am I doing okay so far?" Annette asked Brent.

"You are doing great!" Brent told her.

Annette got a little closer and Brent reached up and grabbed her thigh. Annette teased Brent with the towel. She lifted it a little giving him a brief look under it.

"Are you ready for the stripping? I only have one thing to take off." Annette told us.

"Yes!" We both said at the same time.

Annette, still dancing between Brent's legs, reached to her waist where the towel was folded and let it fall to the floor.