An old rich guy hires a young sexy woman as his housekeeper and personal assistant. She is always naked and having new sexual adventures.
Chapter 25
I wanted to take Maria somewhere for her to show off her body. She’s getting to really enjoy being an exhibitionist. I came up with the perfect place – New York City. In New York, it is legal for women to walk around town topless. A group of women sued the city for discrimination because men could walk around without a shirt but women couldn’t. The court agreed and now women can freely show their breasts around town. The question will be, how much will she need to wear on the bottom? I think it’s legal for women to walk around wearing a thong bikini, so if she can be topless, can she walk around wearing only a thong? I want to try it out with Maria.
I didn’t find out from Maria until after the Scottsdale trip that not only was that her first time on a private jet; it was the first time she’d flown anywhere. I didn’t think we should book a private jet to fly all the way to New York. That seems like an incredible waste of fuel for just two people. Therefore, we’ll need to fly commercial. I imagine Maria’s first time in first class on a Boeing 777 will be just as mind blowing as the Lear was.
We needed to figure out what she could wear on the plane, however. Airlines have gotten really shitty about women dressing in any way sexy for a flight. The problem is that Maria only has sexy clothes. That’s all I’ve ever bought her. I hate the thought of having to buy her something for just the plane flight that she’ll never wear again.
Like Scottsdale, though, I expect she will be able to pack very lightly as she’ll be as close to naked as possible during the day. She’ll just need some slinky stuff for the evening.
We went on-line and looked for clothes for her. We found a dress for her to wear on the plane which wasn’t too sexy but she’d still look terrific in it. She had a couple of outfits she could wear for an evening out in New York, but we added to that with a couple more.
I made our reservations for first-class air seats and a large suite in the Hyatt Regency in Manhattan and I arranged for a car to take us to the airport. Maria was ready with her new dress and heels with a single carry-on bag. Our car got us to the airport in plenty of time to check in. Maria simply stepped out of her heels and walked through the TSA sensor without a problem. After all, all she was wearing was a dress with her naked underneath it.
Being in first class, we were among the first ones to board the plane. We were in the second row and I took the window because it is usually colder at the window and Maria wasn’t wearing much. Her dress was fairly loose on top because she only has B-cup tits. She purposely let one of the spaghetti straps of her dress fall off her shoulder so that the top of her dress gapped nicely. As passengers walked by to their seats, if they looked down at Maria as they passed by, they were able to see most of one of her perfect tits.
During the flight, we got a blanket to cover us which gave me free reign to rub her tits and her pussy throughout most of the flight. I tried to keep her on the edge of orgasm for hours as we flew across the country. Under the blanket, I had one of the straps of her dress all the way down so that the tit closest to me was completely exposed for my fingers to work on her nipple. I hated to have to stop playing with her body when the flight attendant brought our meals.
We landed in New York and took a cab to the hotel. On the way, I had the strap of her dress down and was openly playing with her tit while the driver tried to watch in his rear-view mirror without getting into an accident.
I checked us in and a bellman took us and our luggage up to our room. As soon as we got into the room, Maria grabbed the hem of her dress and lifted the whole thing over her head and tossed it on the bed. Within seconds of getting into the room, she was naked. The bellman was showing me the minibar at the time and when he turned around, he saw Maria standing there naked. Maria just looked at him and said, “I’ve been in this dress all day. I couldn’t wait to get it off.”
I started to reach into my pocked to get out some money for a tip for the bellman when Maria stopped me and said she’d handle it. She dropped to her knees in front of the bellman and reached for his zipper. She looked up at him to be sure he was okay with it and he smiled and nodded. She unzipped and unbuckled his pants and dropped them to the floor along with his boxer shorts. She took his dick into her hand and rubbed it up and down while kissing the crown. She reached up with her other hand and played with his balls and in no time, he was hard as a rock.
Maria slipped his cock into her mouth and went to work on it. She licked and sucked and stroked his cock. She took it out of her mouth, lifted it up, and licked his balls and then sucked each one, one at a time, into her mouth while continuing to stroke his dick. She sucked his dick back into her mouth and licked and sucked it while playing with his balls until he exploded in orgasm and shot rope after rope of cum into her mouth. She kept licking and sucking until she was sure she’d gotten all of his cum.
She sat back on her heels and licked her lips. Before the bellman left, I asked him if he’d like to fuck Maria. Of course, he said he’d love to. I made a deal with him. I had been wanting to find a guy with a really big cock for Maria to enjoy. I told the bellman that if he could find a guy with a big cock of about eight inches to come up to our room and fuck her, that he’d be able to come back and fuck her, too. He wasn’t sure how he was going to go about finding a guy with a big cock. It’s not like he wanted to start asking guys how big their cocks are. I suggested he look for a guy who is at least six feet tall and seems to have big hands and feet. And if he’s a black guy, that might add to the chance he’ll have a big dick.
He told me his name was Sam. I told him to find a guy with a big cock and have him come to our room saying that Sam sent him. If the guy has a big cock and fucks Maria, then he can come back and fuck Maria as well. The bellman thanked Maria for the best tip he’d had in years and left.
Because of the long flight and the loss of three hours on the clock, it was already evening and we were tired from the trip. We laid down on the bed to take a nap and feel asleep pretty quickly. By the time we woke up, it was 9:30 but to our internal clock it was only 6:30 so we started thinking about dinner. Maria didn’t want to get dressed and go back out, so we ordered from room service.
Of course, Maria answered the door for room service completely naked. To her disappointment, though, the room service person was a female. She looked to be in her twenties and wasn’t bad looking. She must have seen a look of disappointment on Maria’s face and said, “What’s the matter? Were you hoping for a man to bring your food?”
Maria replied, “Well, it is usually more fun as I give really good tips.” The room service girl surprised us by saying, “Oh, so I guess you don’t give such good tips to women then? That’s too bad.”
“Oh, I can give a great tip to a woman, if she wants me to,” said Maria. “It’s just that the men almost never refuse my tips but only some women like them. I’d love to give you a nice tip, if you’re interested.”
The room service girl said, “Well, it would be a first for me receiving such a tip with a man in the room, but I’m game if you are.” Maria smiled and walked up to her and hugged her. The girl was wearing a dress which zipped up the back. She would either need to just pull up the dress or take it off. Maria made the choice for her by going to her back and unzipping the dress and pulling it off her shoulders before she could say anything. The girl was wearing a plain, white bra holding an impressive set of tits and bikini style panties.
“Can I take off your bra so I can see these great tits of yours,” Maria asked? The girl looked at me and thought for a second and nodded. The bra was the kind that hooked in the front. Maria undid the latch and two large breasts popped out. Maria let out a ‘wow’ and went to work licking and sucking those big tits.
After mauling the tits for a bit, she put her fingers into the waistband of the girl’s panties and slowly pulled them down until they dropped to the floor and the girl stepped out of them. The two women were both now completely naked and, once again, Maria went in for a hug but this time they were rubbing their two naked bodies together. Maria kind of pushed her down so that the girl was now sitting on the bed. Maria dropped to her knees and spread the girl’s legs to look at her shaved pussy. The girl had just a small patch of closely cropped hair above her slit, but the rest was shaved smooth.
Maria buried her face between the girl’s legs and started lapping at that pussy. In no time, the girl was moaning and whimpering with pleasure. While her pussy was being eaten, she grabbed at her tits and rubbed them and pinched and pulled on her nipples. The two of them completely forgot I was in the room. Once that pussy was really wet, Maria introduced two fingers into the pussy and searched out the g-spot. It was obvious from the girl’s reaction when Maria found the spot. Maria licked and sucked the girl’s clit while rubbing her g-spot until the girl screamed and started shaking in orgasm. It seemed to last a long time, so I’m sure it was a good one.
When the girl had calmed down, Maria was slowly licking up and down the girl’s labia and occasionally dipping her tongue into the girl’s vagina to find any left-over pussy juices. Once Maria was done, the girl just laid there on the bed trying to get herself back together. “Wow,” she said, “you do give good tips. I didn’t realize how much I needed that. Thanks.”
Maria replied, “Believe me, it was my pleasure. You have a lovely and tasty pussy. I’ll be glad to lick that for you any time. We’ll be here for the next four days. Don’t be a stranger.”
The girl finally got up and got herself dressed again. She gave me kind of a sheepish smile as if she’d just realized that she had gotten naked and licked to an orgasm with me watching. As she was leaving, Maria invited the girl to come back in about an hour to pick up the dishes. She said she would.
We ate our dinner and relaxed for a while. Maria had my dick out and had gotten me nice and hard when there was a knock on the door. Maria jumped up to answer the door as I tried to stuff my dick back into my pants. The room service girl came in and started gathering the dishes onto the cart to take out. While that was happening, Maria got on the bed, spread her legs and started playing with her pussy while watching the girl work. The girl kept looking up at Maria as she worked. When it looked like she was ready to leave, she went over to the bed and got down on her knees. She grabbed Maria’s legs and pulled her to the edge of the mattress. The girl buried her face into Maria’s pussy to return the favor from earlier.
I was watching her eat Maria’s pussy and I, subconsciously, started rubbing my still hard dick over my pants. It was so hot watching the girl pull Maria’s legs over her shoulders so she could bury her face further into Maria’s pussy, that I finally pulled out my dick and started stroking it. After the girl had brought Maria to a nice orgasm, she got up, wiped her mouth with the back of her hand and turned around. She saw me stoking my dick and smiled. She said, “There you go. I got her all warmed up for you.”
She wheeled the cart out the door as I continued to stoke my dick and Maria laid on the bed with her eyes closed in satisfaction. It was a great start to our New York vacation.
Chapter 26
The next morning, I called down to the concierge to ask about the hotel’s rules about topless women walking around. I was told that women could be topless in the lobby and the pool and gym facilities. Women, as well as men, must wear a shirt in any of the restaurants. She told me that that is true in most of New York City. Most stores allow a woman to be topless, but restaurants all require shirts. Basically, the law is that anywhere a man can be topless, a woman can too.
Maria put on one of her tiny skirts which barely covers her butt when she walks along with a loose tank top and a pair of heels. The tank is loose enough with large arm holes to provide nice side boob views as well as easy views down the from the top.
We went downstairs and had breakfast in the hotel coffee shop without any problem. Of course, Maria wasn’t wearing a bra or panties as I don’t allow it. With the short skirt and her legs open, her lovely bare pussy was available for anyone to see. Once we left the coffee shop, Maria slipped off the tank top and handed it to me. I had brought along a plastic bag and put the top in the bag and would carry it with us for Maria to slip into at any time she needed to.
She proudly walked through the hotel lobby wearing nothing but a tiny skirt and heels and we walked out onto Broadway. We spent the next several hours walking around town with her perfect tits leading the way. Being typical New York, while the streets were steaming with people, most did not pay any particular attention to Maria’s tits.
Also, as is typical, wherever there was a man in a hard hat working for the city or construction, there were wolf whistles and comments. There was one particular time that some guys were working in a sewer with a guard rail around the manhole. A guy wearing a hardhat was sticking up out of the hole and made a comment to Maria. Maria walked right over to the rail so that she was just a foot or two away from a guy whose head was at street level. She said hello to him as he looked up right at her bald pussy under her skirt. She asked him if he enjoyed the view and he assured her that he did. She parted her legs a bit to give him an even better view and then turned around. She bent down to supposedly adjust her shoe which lifted her skirt up over her butt and gave the worker a great view of her smooth butt cheeks and her wet pussy. Maria finally straightened up, turned to the guy and gave him a wink, and then came back over to me and we continued our walk. She’s such a wonderful tease.
We found a nice deli with outdoor dining so that Maria didn’t have to put on her top. We had a great lunch while Maria sat facing the sidewalk with her legs open showing off her pussy to anyone walking by.
We did a lot of window shopping and did go into a few stores to see if we had any problem with Maria being topless, but had no issues. Maria’s feet were starting to hurt after walking for hours in her heels so we decided to get a cab back to the hotel. Now, even though there are a lot of cabs in New York, it usually takes a while with your hand up to get a cab to stop. With Maria’s hand up and her tits sticking out, I don’t think we had to wait two minutes to get a cab to stop.
I opened the back door and before getting in I asked the cabbie if he wanted Maria to sit up front with him so he could get a better look at her tits. He quickly agreed so I opened the front door for her and I got in the back.
Maria asked the cabbie, “Do you get a lot of topless women in your cab?”
“No,” he answered, “I get one every once in a while, but not many women actually walk around town topless.”
“Do you like my tits.” Maria asked?
“Of course. They’re beautiful and the perfect size,” he answered.
Maria said, “I’m having fun walking around topless. I wish I could walk around completely naked. That would be real fun. I’m close to that because all I’m wearing is this short skirt. I bet you’d like it if your passenger was completely naked.”
“Yeah, that would be great,” the cabbie said. “So, you mean you don’t have any panties under that skirt,” he asked?
Maria lifted up the skirt and showed him her bare pussy. “Nope. See? Do you like my pussy? Do you want me to get naked here in your cab?”
“Man, your pussy is as perfect as the rest of you. I’d love it if you got naked.”
Maria pulled her skirt right down and let if fall into the wheel well. She was wearing just a pair of shoes. She turned towards the cabbie and put her back against the door. She lifted her left leg and put her foot on the seat while leaving the right one on the floor to open her pussy as much as possible for the cabbie. Then, she put her hands down to her pussy and spread her labia open to let the cabbie see inside her vagina. “Is this what you were hoping to see,” she asked?
The cabbie was glancing over and back to the street to keep from hitting the car in front of us. He was also rubbing the bulge in the front of his pants. “Your pussy looks so inviting and tasty. You are one sexy woman. Thank you for showing yourself to me.”
Maria saw the bulge in his pants and reached over and grabbed at it feeling his hard cock in his pants. “If you can find a private place to park for a bit, I’d be glad to take care of that hard cock for you, if you want. I don’t want you to think I’m just a cock tease.”
The cabbie didn’t need to be told twice. He made a quick right at the next corner and found an alley and drove down until he could find a place to stop. Maria leaned over and started working his zipper down and he helped to open his pants and pull them down to his knees. Maria stroked his cock a few times and found it was already quite hard and leaking precum. She licked the precum off and then put the whole cock in her mouth and started licking and sucking. The cabbie put his hands on Maria’s head to help make sure she didn’t bang her head against the steering wheel as she was working his cock up and down. It didn’t take too long before he was shooting his cum into Maria’s mouth and she was swallowing every drop.
“Yum, I love your cum. I wish there would have been room for me straddle you and feel your nice cock in my pussy. I’m so wet now,” she told the cabbie. Maria reached down to her pussy and scooped up some of her pussy juice on her fingers. She rubbed her wet fingers around the cabbie’s lips and then slipped them in his mouth so he could taste her pussy. He sucked her fingers clean and told her how good she tasted.
Reluctantly, the cabby pulled his pants back up and tucked his dick back in. He started the cab and drove us back to the hotel. Maria was still sitting in the seat naked when we pulled up to the hotel. The valet opened Maria’s door and Maria swung her legs out, picked up her skirt off the floor and then slipped it on while the valet watched before she got up out of the car. I paid the cabbie and he assured me that no tip was necessary as he’d already gotten one.
We walked through the hotel lobby to the elevators and waited for one to take us up to our room. The doors finally opened and a couple came out who were probably in their sixties. The woman saw Maria and said, “Oh my.” The husband had a big smile on his face. We got into the elevator and the man turned around to see Maria one more time and as he did, Maria lifted the front of her skirt and showed him her pussy as the door closed. I’m sure Maria made his day.
When we got up to our floor and the elevator doors opened, we stepped out and Maria slipped her skirt down and off and handed it to me. She walked down the hall to our room completely naked wearing only her heels. Unfortunately, no one came out and saw that beautiful sight.
Chapter 27
We ate in the room that night. Maria was naked when the room service guy came in, but Maria didn’t offer her body to him. I don’t think she found him particularly attractive. She does love just showing off her naked body, so it was fine.
About nine o’clock that night there was a knock on our door. Maria opened the door and there was a tall black guy standing there. He said, “Hi, my name’s Will. Sam sent me and said you needed some help with that pretty pussy of yours.”
“Well, Will,” Maria said, “do you have a big enough cock for me? I need a big one tonight. Show me your cock and if it’s big enough, I’ll let you in.”
“You want me to show it to you out here in the hall,” he asked?
“Why not,” Maria said, “after all, I’m standing here in front of you naked. Show me your big cock.”
Will unzipped his pants and fished around in his underwear trying to pull his cock out of his pants. He finally pulled out a cock that was at least six inches long and wasn’t yet hard. It also looked really thick. Maria liked what she saw and grabbed him by his cock and pulled him into the room.
She no sooner closed the door and she was on her knees in front of Will with his cock in her mouth. While she was working on him, he unbuckled his belt and unsnapped his jeans and let them fall to the floor. Maria pulled her mouth off the now half-hard cock and pulled off his shoes and socks and pulled his pants off while he took off his shirt.
The guy was built. His muscles had muscles and his cock, which wasn’t quite fully hard yet, was at least seven inches long. Maria went back to work on his cock. Once he was fully hard, she pulled it out of her mouth and was staring at a cock at least eight inches long and at least an inch and a half in diameter.
Maria said, “My God, Will, your cock is perfect. I love it. As much as I want to taste your cum, I need this in my pussy now.” She climbed up on the bed and patted it for Will to join her. “I want to start out on top so that I can get used to the size on my own time before you fuck the shit out of me with that.”
Maria straddled Will and found she had to get up on her feet over him to start lowering down. “Oh, it’s so big. It feels so good,” Maria was moaning. She got to where she could at least be on her knees over him and was working his cock up and down a bit getting more of his cock in with each stroke. It took several minutes before she was finally sitting her butt all the way down on Will’s thighs. She’d taken it all and just sat there and enjoyed the feeling of fullness. Will got tired of waiting and grabbed her by the waist and started raising her and then dropping her on his cock. I was sitting across from the bed and was looking at Maria’s perfect butt bouncing up and down with a big black cock plowing into her pussy. Her inner labia pulled out with his cock each time like it was gripping his cock trying to keep it in her. I had never head Maria make the sounds she was making now. She was clearly in fuck heaven.
Will grabbed her hips and then flipped them over so she was on her back and he could start really driving his cock into her as hard as he could. She kept asking for more and harder. I could see her grimace a bit with each pound of his cock as he was probably hitting her cervix with each thrust. “It hurts so good,” Maria panted.
Will had amazing stamina. He just kept ramming into her over and over again. He finally pulled out, flipped her onto her stomach, pulled her hips up in the air and plunged back into her pussy from behind. Maria let out a scream as he hit even deeper in her and was really pounding her cervix. She started begging him for his cum and he finally tensed up, slammed his cock all the way home while pulling her ass back into him and he unleashed his load of cum into her pussy. I could see his butt clench with each pulse of his cock. It seemed to last a long time so I assume he gave her a really big load of cum.
Maria collapsed down onto the bed and Will landed on top of her back. Once his cock slipped out of her pussy, he rolled over to the side. Maria had caught her breath and turned to him and grabbed his wet cock. She lifted it and started licking his balls clean. Once they were clean, she started to lick his cock when she stopped and asked Will, “Would it be okay with you if Joe helps me lick your cock clean? I’ve always wanted to see him lick a nice cock.”
That surprised me, but I was certainly okay with it. I’d told Maria before that I’d do anything she wanted sexually as long as the other person was okay with it. Will said he didn’t have a problem with it so I joined them on the bed and Maria pointed Will’s cock at my face. I stuck out my tongue and gave his cock a lick. I don’t mind the taste of cum, especially when it’s mixed with Maria’s pussy juice. I’ll lick it out of her pussy, there’s no reason not to lick it off a cock. Maria said, “Lick it, Joe. Suck his cock. I want to see you suck Will’s big cock.”
It was a good thing that Will’s cock wasn’t hard because I don’t think it would have fit. I couldn’t believe how big it was when it was soft. I licked and sucked his cock clean while Maria watched me intently. She was rubbing Will’s balls the whole time I was sucking his cock. I felt him start to get harder and he was filling up my mouth more and more. I finally had to pull off of him because I couldn’t handle any more.
Maria started stroking Will’s cock and told me to lick her pussy clean. She got up on her knees over Will to look at and lick his cock while I got under her and she plopped her dripping wet pussy on my face. Almost immediately, there was a flow of cum that came out of her pussy into my mouth. I don’t know why I love licking cum out of her pussy so much but that seems to turn me on more than anything.
I licked and sucked at her pussy for several minutes until I’d gotten every drop of cum out of her that I could. Will’s cock was now at full staff and ready to go again. Maria jumped off the bed and took Will’s hand and pulled him off the bed and led him into the bathroom where they took a long shower together. From what I could hear, he fucked her really well again in the shower.
Will had probably been in our room for over two hours when he finally got dressed and left but not before he and Maria kissed like two long lost lovers. Maria was clearly bummed when Will finally had to leave.
After he’d gone, Maria thanked me for setting that up. She said it was the best fuck of her life and now she understands the phrase, “once you try black, you don’t go back.” She wants to find a guy like Will back home to come in a couple times a month to fuck her really hard and long. She told me that Will’s cock was hitting her cervix so much with each stroke. And when in the doggy position, his cock was actually penetrating her cervix into her womb. She said it was the first time in her life that she wished she wasn’t on birth control because she had an overwhelming desire to be bred by that big hard cock in her womb.
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