Andy and Stephanie Pt. 03

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Ass

The next morning, Andy woke up early and grabbed a quick breakfast in the hotel before heading to the shuttle.

The volunteer cleanup crew consisted of locals and tourists, about half of both. They drove an hour and a half from Montego Bay through the mountains to the town of Crawford on the other side of the small island. The devastation wasn’t the worst Andy had seen, but there was a lot of work to do. He worked with some of the other volunteers to remove debris from a road until lunchtime. After lunch they went into a hospital and cleaned out the ruined equipment and furniture from the first floor until it was 5:30 and time to head back to the hotel.

Meanwhile, as soon as Stephanie woke up, she texted Jamal and he came over.

“I got bad news for you…” he announced.

“What? Don’t tell me you forgot the key to the chastity cage.”

Jamal chuckled, “no, I have that, but I forgot condoms…”

“Are you serious? Ugh. Well…I haven’t been with anyone else bareback…so I guess its safe. I know Andy brought some for himself…I’m sure those won’t fit on you but at least he’ll be protected. I need your dick. Let’s do it anyway.”

The two ordered breakfast in bed and made love all morning. Stephanie came four times and Jamal dumped a load in her pussy and another all over her face.

They spent the afternoon lounging by the pool sipping cocktails. Around 3pm a tall black man in a white linen suit approached them.

“Good afternoon, are the two of you having a pleasant stay at the resort?” He asked.

“We’re having a great time!” Stephanie responded.

“I’m glad to hear that. I’m the owner of the resort, and I must say, seeing the two of you here enjoying our property and looking so incredible made me realize that you are exactly what we want for our brand. I have a proposition for you. You will allow us to take some photos of you enjoying the resort and use them in our promotional materials. In exchange, we’ll upgrade your room to the plantation mansion. You can spend the rest of your stay there at no additional cost, and enjoy the numerous amenities that part of the resort has to offer, in addition to everything you have access to now.”

“Wow! That sounds so exciting!” Stephanie was four drinks in and the prospect of spending the remaining nine days in a mansion was thrilling. “What do you think, Jamal?”

“That sounds great.”

“Wonderful!” The owner responded. “I’ll have the bell hop move your things. If you’re ready now, you can follow me over to the mansion and I will give you a personal tour.”

The plantation portion of the resort was even nicer. It was less crowded, and featured 4 pools and a private beach. With manicured lawns and staff everywhere catering to guests’ every need, Stephanie knew she would enjoy the upgrade. The mansion itself was huge, with a glorious master suite, a library, an indoor swimming pool, jacuzzi tub, a separate bedroom with a waterbed, and even a sex swing. Outside was a private pool surrounded by hedges, a private beach, and another sex swing.

“I’ve shown you the entire part of the mansion that you’ll have access to. There’s also a large kitchen, and we have dedicated staff that can cook up anything your appetite desires while you’re here,” the owner explained.

The staff was dressed differently than in other parts of the resort, with the men wearing butler style suits and the women wearing French maid’s outfits.

“There are two key people on the staff that you’ll interact with. First is the butler, he’s in charge of the entire operation. And second is the maid, who will take your orders for meals, clean up after you, and generally see to any requests you have during your stay.”

The owner left, and soon their luggage arrived.

“Let’s try out the sex swing next to the pool!” Stephanie suggested.

Sex with Jamal was always amazing but the sex swing brought it to a whole new level as they were able to hit different angles with Jamal’s 9″ cock. Stephanie came three more times before Jamal deposited yet another load into her married pussy.

“I wonder when Andy’s coming back…he’s going to love this mansion!” Stephanie thought.

Two-thirds into the 90-minute bus ride back to the hotel, traffic came to a full stop. After about half an hour, the driver made an announcement.

“Bad news folks…it looks like a bridge up ahead has collapsed. We’re going to have to go back to Crawford and find another way home.”

Andy teared up. It was 7pm, and they had reservations at 8pm. He’d be lucky to make it back by midnight. Not only would he miss out on the dinner with his wife, but he would have to wait one more day to consummate his marriage.

At 8pm they got back to the hospital they had cleaned up in Crawford. The driver informed them that the alternate route was 3 hours long, driving along the coastline, but there was too much debris in the road from the hurricane. They could make the trip, but they’d have to make frequent stops bahis siteleri to clean up. They also couldn’t do it at night, due to safety concerns and the difficulty of cleaning debris off a road in the dark.

Andy found a motel to spend the night, and a payphone to call Stephanie at the room at the resort. He didn’t even bring his cell phone since he didn’t have service. She didn’t answer and he left a voice message on the machine.

Meanwhile, after fucking Jamal on the sex swing, Stephanie called the front desk to inquire about the bus. While they didn’t know the specifics of the trip, they informed her that the bridge had collapsed and it was highly unlikely that they would be able to return tonight.

Stephanie was looking forward to a romantic dinner with Andy, but not to having sex with him, so she felt a mix of disappointment and relief. The good news was that Jamal could accompany her to dinner and she could have more great sex that evening.

They made their 8pm reservation and after a leisurely and delicious two-hour five-course meal, they retired to their mansion and made love in the waterbed before falling asleep in the master suite.

The volunteers gathered at the bus at 8am the next morning, and they proceeded to Montego Bay. They had to stop 6 times to clear debris and finally made it back at 2pm. Andy was starving and exhausted. He didn’t bring his room key, so he hoped that Stephanie was in the room. When he knocked, no one answered, so he walked around the resort looking for her. After about an hour he tried knocking again, with no response.

He went down to the front desk to ask for a key, but when they asked him to verify his identity he realized he didn’t bring his passport. The clerk was kind but stern, and refused to give him a replacement key without his ID. He produced a credit card, and convinced her to take that as proof of his identity, but when she looked him up in the system, his name wasn’t on the reservation. Stephanie made it and she never added his name.

Andy sighed and walked away to look for Stephanie more. He walked over to side near the plantation mansion, and admired the mansion and the private beach about 150 yards away. There was a beautiful woman in a white bikini tanning on the beach. He thought she looked like Stephanie, so he started walking over there. As he approached the entry to the plantation section, a security guard stopped him.

“Room key, sir?” he asked.

“I don’t have mine, but that’s my wife tanning on the beach and I’ve been looking for her, since she has my key.”

“I’m sorry sir but you need a key to get in. And that woman has been with another man this entire trip, so I don’t think she’s your wife.”

Confused, Andy walked away. He was stuck. The only thing he could think of to do was to wait until late evening when his wife would be in her room getting ready for bed, and call then. Otherwise he was almost out of change for a pay phone and he couldn’t afford to keep calling. Shaking his head, he left the resort and went to a restaurant to wait out the afternoon.

Stephanie split her time between the beach and the pool, enjoying the poolside service and privacy. Jamal went golfing and spent the afternoon reading by the pool. They knew that Andy could return at any time, but also that he would have no way of getting to the mansion, so they could simply wait until he arrived at the front desk and the staff would notify them of his arrival, to ask permission that he be allowed in the mansion area. Of course, they were unaware that Andy’s name wasn’t on the reservation and he was persona non grata as far as the staff was concerned.

Jamal and Stephanie enjoyed an 8pm lobster dinner served on their private balcony overlooking the ocean. After dinner they retired to the bedroom where Stephanie sucked Jamal’s long black cock hard before riding it. Just as he was about to bring her to her first orgasm, the phone rang.

“Do you want to get it?” Jamal asked.

“No, no, keep fucking me with your big cock!” Stephanie yelled.

“It might be Andy.”

“No, don’t stop, yes, that’s it, yes!” Stephanie exclaimed as she erupted in her first orgasm of the night.

At 10pm Andy figured Stephanie must be in the room by now, so he called the hotel and asked to be transferred to her room. The phone rang and rang and he left a voicemail. Disgusted, he stormed over to the hotel. He was not spending the night in a motel.

“Look, my name is Andy Johnson and my wife is Stephanie Johnson and I don’t have my room key and I just need to get into the room. I’ve been locked out all day.”

“I’m sorry sir, do you have an ID?”

“I have a credit card with my name, but I’m not on the reservation. Please just give me a key to Stephanie Johnson’s room. She’s my wife.”

“I’m sorry sir we can’t do that.”

Andy raised his voice, telling the clerk he was paying for the room and demanding to be given a key. He was getting unruly, and security came in and escorted canlı bahis siteleri him outside. He was told he was permanently banned from the resort.

Around midnight Jamal and Stephanie were done fucking and Stephanie answered the voicemail.

“That was Andy. He called from a payphone nearby. He said the hotel won’t let him in!”

“Ahh, well that makes sense. I was wondering what happened to the poor dude,” Jamal said.

“He asked me to tell the front desk to let him in.”

Stephanie called the front desk. They told him about how Andy had been kicked out of the hotel.

Crying, Stephanie explained everything to Jamal.

“Can you fix this? Please…I feel so bad for him.”

Jamal went to the front desk and said that he was a friend of Andy and Stephanie’s. He explained what happened. They told him they took their lifetime bans seriously.

“Is there anything we can do to get him to be allowed to return to the hotel.”

“Well…” the manager said, “this is a little unconventional, but we are short staffed for the mansion, actually. You have seven days left in your stay, if he agrees to serve on staff for five of them, he can enjoy the final two as a guest. There’s an old servant’s quarters next to the master suite in the mansion where he can sleep. There should be a uniform there too. That’s the best I can do. If he agrees, he needs to report here in uniform at noon sharp tomorrow.”

Jamal and Stephanie agreed that sounded like the best possible solution. She called nearby motels until she found Andy.

“Andy!” Stephanie exclaimed. “Oh, I’ve missed you so much! I’m so sorry for everything that you’ve had to go through. Look, I have good news…kinda. I got the hotel to let you back in…but you have to serve on staff for five days then you can enjoy the resort for the final two. That’s the only way they’ll forgive your lifetime ban.”

“Wow…really? You explained everything to them? Fuck, I mean I was out helping their country recover from this hurricane.”

“I know babe, I know. That’s just how it is. In other news, we got upgraded to the mansion! It is amazing. You’re gonna love it.”

“Wow!” Andy exclaimed. “So was that you I saw making out with a black guy yesterday…” he thought.

“So why don’t you come here at 10am and we’ll talk and reconnect and then get you ready for your shift? Sound good?”

“Okay. But what about the cage? When can we have sex?”

“Andy, I know it has been hard having your little thing locked up for…what is it now, three months? But you need to stop asking. I know you’re in it, I know you want to get out, and I’ll decide when the time comes. You got that?”

“Fine. Goodnight,” Andy hung up.

Andy arrived promptly at ten the following morning and Stephanie greeted him with a hug and a kiss and escorted him to the mansion. When they arrived, Andy asked how they got the upgrade.

Stephanie led him to chairs in the living room downstairs.

“Andy, there’s something I need to tell you…when I was a sophomore in college I became addicted to sex. To fucking athletes. I went through most of the basketball team and part of the football team. I had sex with some non-athletes too, but never more than once. They never compared. When we started dating, I was madly in love with you, but I didn’t want to have sex with you because I knew it would disappoint me. And when you sent me that dick pic…I knew you didn’t have the equipment needed to please me. Babe, I tried so hard. I got that dildo that’s your size just to see if I could enjoy being with you in that way but I couldn’t even get close to feeling the pleasure that I feel with a bigger guy. I’m sorry but I can’t give it up. I’m an addict.”

Andy stared at her, dumbfounded.

“So…uh…what does this have to do with the mansion?”

“Well, I knew I couldn’t do this trip without some real fucking. I knew you’d disappoint me. So I asked Jamal, you remember Jamal? The forward from the team in college? Anyway, I asked him to come down and hang out with me here. So while you were gone we were lounging by the pool. The owner came up to us and said he wanted to use us as marketing material for the resort, and in exchange he’d upgrade us to the mansion. We thought when you came back they’d tell you, but obviously that didn’t work out.”

“So wait…this whole time I’ve been cleaning up debris and staying in motels and you’ve been screwing Jamal?”

“Umm…yeah…and one other thing…Jamal?”

Jamal walked in, and sat next to Stephanie on the couch. Shirtless, his 6’7 muscular frame towered over the white couple. He was wearing only a pair of light blue, tight-fitting swim trunks, and his ample bulge was apparent. At 6″ in flaccid length it was quite hard for him to hide his bulge even when soft.

“Tell him about the key,” Stephanie commanded.

“So…I keep the key to your chastity cage now. I’ve been keeping it since you got back from your honeymoon. Stephanie gave canlı bahis it to me so that I would fuck her. I’m leaving on the day your punishment is over, and if you behave yourself, I’ll leave the key here so she can unlock you.”

It was finally settling in for Andy. He hung his head in shame and a tear dropped onto his lap. Stephanie came over and hugged him, telling him that she loved him and why, and that she wanted to spend the rest of her life with him. He recovered, and it was time for him to get ready.

“So if you go outside, there’s a staircase around the back that leads up to the servant’s quarters. That’ll be your room, and they told us there’s some uniforms in the closet for you to wear.”

Andy went upstairs and peered in the closet. There were uniforms, but only the maid style outfits the female staff wore. He went back down and informed Jamal. Jamal called the front desk, who reminded him of their deal and said that was all they had.

“Andy, those are the only uniforms they have. The clerk at the desk suggested you shave your legs and put it on or she can send security here to escort you out. Stephanie can help you shave your legs, but you’d better be quick.”

Andy rushed to the bathroom and Stephanie helped him shave his entire body.

“You look almost like a girl now! And look at that cute butt!” She said as she smacked him on the ass.

“Now, for the outfit…I think you’re probably a size medium. I’m worried about your underwear – boxers will definitely not work with this skirt. Just a minute, let me ask Jamal what we should do…” she left the room, returning a few minutes later. “He says you definitely need to be wearing something underneath the skirt, so if your boxers don’t work, then you should wear a pair of my panties. I think they’ll actually fit you quite well.”

Stephanie grabbed a pair of grey boyshorts. “I didn’t bring enough for two, so you’ll have to wear my dirty ones. Luckily for you, the first pair is pretty androgynous.”

Andy put them on. They were snug around his cock cage, but otherwise they fit quite well. He donned the rest of the maid’s outfit: 3″ heels, tights, and a dress featuring a flared mini skirt.

“Perfect! You look almost like a short haired woman!” Stephanie exclaimed with a giggle. “Now report to the front desk for the start of your day.

Walking in heels was a real challenge. Andy felt ridiculous in the outfit but surprisingly the guests hardly noticed him. His assignment for the next five days was to fill in the maid role in the mansion, seeing to whatever needs the guests had. It dawned on him that the guests were Stephanie and Jamal: he would be serving his wife and her lover.

After a quick briefing, he scurried back to the mansion to take their orders for lunch. Stephanie and Jamal were lounging by the pool, and he quickly put their meals in and served their drinks.

The butler, his boss, was a man named Charles. At a stocky 6’1″ he was intimidating and Andy hoped to remain on his good side.

As he served Jamal and his wife, they treated him like they would any other staff member. It was gratifying that they weren’t making fun of him, but humiliating that they paid him no more mind than they would anyone else. After lunch, Charles instructed him to go clean the bedrooms. The master bedroom was relatively orderly, but the second bedroom with the waterbed was a mess. The sheets were covered in cum. Andy didn’t know it at the time but not only was Jamal’s cum on the sheets but Stephanie’s squirt was as well.

Andy finished cleaning the bedrooms and went outside to clean up from lunch. He was shocked to find the two of them fucking on the sex swing next to the pool. While Andy wasn’t very close to them, he could tell that Jamal’s cock must be quite long by the long strokes he was doing. Although their area of the resort was very private, surely other guests could hear Stephanie’s loud moans of pleasure as Jamal pounded his 9″ black dick inside her. Of course, Charles could see it too and Andy was extremely humiliated by that because Charles knew that Andy was Stephanie’s husband.

It didn’t get any easier for Andy, for his evening was spent serving dinner to the two lovers on the beach. His skirt swished as he went back and forth from the kitchen to their table on the beach in his 3″ heels. Eventually, they were done with dinner. As Andy cleaned up, Stephanie knelt on the sand and started slurping on Jamal’s thick cock. When Andy would pass by she looked at him, giggled, and winked.

The two retired to the master bedroom shortly after, and Andy finished cleaning up at 11pm and went up to his servant’s quarters. It shared a wall with the master bedroom but had a separate entrance and was not connected to the guests’ part of the mansion. He soon realized that Jamal and Stephanie were making love: he guessed from the slurping sounds and Jamal’s moans that she was giving him another blow job. Before he could fall asleep, they started fucking, and he soon realized that sleep was not in the forecast as long as they kept going at it. The bedframe was hitting the wall, and Stephanie was screaming his name.

“Fuck me with your big cock! Yes! Mmm, fuu-uuu-uuck me Jamal!” She yelled.

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