Chapter 3

It felt like the first day of school when I was saying goodbye to my mom. She gave me a hug, stood back and looked at me. She warned me to be safe, have fun and call from time to time. I took a cab over to the Gracie mansion and checked into the Master Suite. I rode with the town car to the airport and went inside with the sign while the driver stayed with the car.

Tiffany was wearing a sundress as she came down the escalator. I got a hug from her and we got her bags. On the drive into the city, we talked about her flight up and packing for such a long trip. I assured her that she could have brought two sets of clothes and they’d always be clean. We could have laundry done every night if we wanted.

When we got into the room, I told her to unpack her things and then we’d talk. She admired the suite as she went to the bedroom. There was a bar but not a full kitchen like the suite in Chicago. We looked out at the river and the park beside the property. When her clothes were put away, she came out and asked, “Why did I just do that when we’re leaving to go overseas?”

She sat down and I said, “Tiffany, can you tell me what Jody told you and what your expectations are while we’re together?”

“She said that it was like a dream come true. She was a princess and you were her prince until the clock struck midnight and it was all over.”

“What were your ideas before she called?”

“That I’d get to see the Louvre and some other sights by day and be your sex slave at night.”

“I wanted to set your expectations before we left. Jody had just turned 18 and sexually was very inexperienced. You’re older, more mature and more sexually experienced. My expectations for you are higher. You’ll be my sex slave twenty-four hours a day, seven days a week. You’ill also be treated like a princess, stay in nice hotels, eat great meals and get guided private tours of wherever you want to go. Think of the best and worst and multiply it by ten.”

She sat quietly and tried to absorb what I’d just said. She looked up, “Can you give me an example of the worst?”

“You’re a beautiful woman but you have what, an A cup or small B cup breasts?”

“Right about there.”

“I plan to leave many of your clothes here. You can trash them or we can pack them away for you to pick up on your way home. I don’t think I’ll let you wear a bra most of the trip. We’ll be gone for two months. That means two periods for you. That means that I’ll only have your hands, mouth and ass during those times unless I’m in the mood to get messy and just fuck you and clean up later. I’ll use all three holes before we leave New York. Did Jody tell you about her toy?”

Blushing, Tiffany said, “I sometimes go without a bra so I can live with that and would want to see what clothes you didn’t want me to take and then decide what to do with them. I figured that you’d use both my mouth and pussy. My ass was 50/50 in my mind. Jody told me about the vibrator and having to perform for you. I can see where that might be exciting for both of us and I’ve come to grips with that.”

“I might bring another woman to my bed, our bed or your bed so that I can watch. Right now minimum wage is $4.15 an hour. This trip will cost me about $150,000 so your half is about $75,000. This room is about $400 a night. We’ll travel first class on any plane, train, boat or car. We’ll eat at the best restaurants that meet our demands. We had pizza in Chicago one night and ate at Mortons the next. Jody was dressed appropriately and the only clothes she wore that were hers were the ones she showed up in. She came home with artwork, new clothes and a new vibrator. If I tell you to go pick up a woman and have sex with her, you can call a hooker or seduce one at the bar but I expect you to obey. I’m sorry to be blunt and ruin the beginning of your fantasy but I want us to be crystal clear on expectations.”

“I think that’s fair but I may need help if I have to seduce a woman. Most men would be easy. I had high hopes when I spoke to Jody but when I wrote the letter I had an idea of what this could look like for me.”

“I thought you were more mature and would see my logic.” I want you to take a suitcase or both if you need them and sort through your clothes. Everything you plan to take with you, you’ll model for me. If I don’t like what you show me, I’ll rip it from your body and punish you or make you perform for me. You have a package on the table, similar to the one that Jody received.”

“Yes, Sir.”

She went into the bedroom and was there for almost 30 minutes. She came out wearing the same clothes she flew in and hadn’t changed. They were nice but were of a lesser quality. “I filled my bigger suitcase with things I’ll leave here. I have a few things that I think will be good for the trip.”

I stood and walked over to her. I started to unbutton her top. She grabbed my hand out of reflexes but soon let go and apologized. She was wearing a bra. The top was okay but a little baggie on her. I took both of my hands and all the buttons popped off as I pulled open her top. The bra was white cotton and it was soon hanging open in front even though it was a back clasp.

I lifted her skirt and she had on white cotton comfortable panties. They were soon on the floor. The skirt was okay and I left it while tossing the rest of her clothes in the trash. “I hope that the others that you kept are going to pass inspection better than this outfit. It’s not too late to walk out of the room naked and ask me to dress you. Although you do have a skirt and that could be fun. I like having access to your pussy.”

She went back into the bedroom and after about ten minutes, I followed her in. She was still in only her skirt and had most of her second suitcase full. Looking up she said, “I don’t know what you’re looking for and don’t want to ruin any more.”

I took her hand and stood her up. I gave her a gentle hug and her nipples felt good along with her small but firm breasts. “We’ll figure it out Princess. We should probably have sex and then go shopping and get some food in that order.”

“We can do that.” She said, I put the suitcases to the side and she removed her skirt to be standing there nude in front of me. I was happy to see that she took what Jody had told her and trimmed the top and shaved the bottom. “I see that you took notes from Jody,” I said as I started to undress. She took some initiative and started to rub her slit while I got undressed and when I was naked, I kissed her hand before eating her pussy until she came. After that I moved up her body and said, “Put your new Master’s cock where it belongs. In his new pussy.”

She tensed a bit but lined up the head of my cock with her wet opening and soon we were having sex. It didn’t take long for me to be ready to fill her. I thought about pulling out and shooting all over her but didn’t want to make any more of a mess. I filled her and then held her for a bit as we both got our breathing under control. I said, “That wasn’t too bad was it?”

“Do you mean the first time cheating on my husband, knowing that I’ll be doing that a lot over the next two months or knowing that I just had the best sex of my life and it was just a quickie for you? I feel very confused about my emotions and excited about the future.”

“Go get cleaned up and we can go shopping.”

“Yes, Sir.”

“That isn’t the first time you called me, Sir. Is that common for you?”

“In class sometimes I’ll call the student, Miss Smith or Mr Jones. But you’re the only one I’ve called Sir since grade school. I think it fits you and your position. Do you want me to stop?”

“No, I like it. You can call me Brad, Sir, Master or anything that isn’t said in a negative way.”

“Sounds good, Stud.”

When she came out there was a t-shirt and her skirt. She had on a pair of sandals. She dressed and didn’t ask about panties or a bra. I just smiled and took her hand as we walked down the staircase and out to our waiting car. We didn’t go to the department stores but went to the designer stores and slowly but surely built a wardrobe that would last a few days until we made it to Europe and had time for other shopping. She got a few thongs but no bras. She also got a few second glances and more than a few smiles. She was just smiling back by the time we were done.

The packages minus one thong, a new dress and pair of heels were sent back to the hotel with the car and we were dropped off at the Oak Room for dinner. We sipped martinis and she talked about the shopping and the prices. The service was like nothing she’d dealt with before. We had some oysters to start the meal and being from Florida she was used to them and enjoyed them.

The oysters were followed by small Caesar salads and then I had the prime aged burger and she had the rack of lamb. She laughed that I’d order a burger at such a fine restaurant until I cut off a piece and made her try it. She changed her mind but enjoyed her lamb. We both had coffee and Brandy after dinner and she glanced at the bill as I signed and put my card away.

“So this is how the other half live?” she asked.

“I don’t know about the other half but maybe the other five percent. Many can afford to live like this for a lifetime dream vacation or a special dinner out. To do this day in and day out, it means that you don’t worry about money for your next meal, or your next car. It’s all in the checking account. A new home you may have to move some investments around but you don’t talk about mortgages and giving the banks a nickel in interest.”

“I hope I don’t get too used to it but that’s part of the package I signed up for. What’s next?”

“I said that I’d take all three holes before we left the country. How long did you want to stay in New York?”

“Didn’t you book flights and hotels?”

“There’s always room on a flight for the right price. There are plenty of hotels in any city. I tend to stay at the Kensington Collection of hotels if there’s one available where I am. We may need to take a taxi from time to time. As long as your passport is good and you aren’t wanted we should be fine.”

“Let’s go back to the room and let me suck you off before you fuck my ass. Do you have any lube?”

“There’s some in the package you didn’t open yet.”

She sucked me off and then we spent a while getting her calm enough and relaxed enough to take my cock. I won’t say she loved it but was doing alright when I was rubbing her clit and came deep in her ass.

“It hurt when you did that. You’re much larger than my husband. And much larger than is meant to be in my ass. Thanks for taking time to let me adjust.”

“I’m not out to hurt you. Except if you need spankings but even then it would just be to train you. Are you going to be alright?”

“I’ll be fine. Where are we going first?”

“Where do you want to go first? Iceland, Amsterdam, London, Ireland?”

“Iceland would be cool. Is there anything to see there?”

“Nature. They have some beautiful places to see and explore. Volcanoes, geysers, hot springs, waterfalls, and glaciers. You don’t have a bathing suit or proper clothes but we can always shop for you. There are no famous art museums there but it’s a fun place to explore.”

“It sounds very diverse and beautiful.”

“I’ll book us a flight this afternoon and you can get a bikini, and warm clothes. I didn’t buy you a suitcase yesterday so we should get you a bag as well.”

We did all those things in the morning before heading to the airport, landing on the last flight into Reykjavik. My travel agent at the hotel headquarters booked me into the Reykjavik Residence Hotel. It was nice enough but a step down from the Kensingtons. We found a little pub and had some dinner. The Islenski Inn and bar had dried shark, lobster, lamb and many other unique dishes. I had smoked salmon on rye bread that was very good.

We talked to a few locals and had a good time over drinks. We didn’t speak Icelandic but most of them spoke English which was good. They talked us into trying a shot of Brennivin and then we switched to Reyka, a local vodka that was very smooth. From the Oak Room to the pub in Reykjavik drinking vodka martinis.

The next morning we got up and went to the Blue Lagoon, a local hot spring and enjoyed that heated water and light fog over the surface. It was a fun and unique experience. We had a driver take us around the Golden Triangle and visit the most common attractions. We found another pub that night and had some good food, good drink and were in bed and having sex before the pubs closed.

Day 4 Tuesday We flew out early the next morning to Amsterdam. The city of canals. The waterways and old architecture make it a city to behold. There’s a Kensington hotel in the city so we checked into the Hotel Ambassade’s Grand Canal suite. We put down our luggage and I unzipped my pants. She smiled like a fox and asked, “Which hole do you prefer, Sir?”

“Get out your toy and use it on your cunt while you suck my cock.”

“Yes Sir. May I cum when I’m ready?”

“You can cum with me or after me. If you cum before me I’ll pull out and paint your face. You’ll wear it until dinner time.”

“Yes, sir.”

She seemed happy and was enjoying her role. She put the toy in her pussy after getting completely naked and then took me in her mouth. She turned on the toy but the hum from her mouth was as loud if not louder than the toy. She used one hand to move the vibrator in and out of her cunt and the other to stroke the shaft not in her mouth or play with my balls. She was on her knees and I reached down and took her arm that was holding the vibrator.

Until then she could control the movement and thus control her orgasm. I took her hand and put it behind her head as I pushed her down to the floor pushing the vibrator up into her pussy and pressing against her cervix. I also pulled her face onto my cock. The new pressures and loss of control, made her panic some and she started to suck more and stroke more to get me to go first.

“Every slut has a plan until her master changes the rules. You’d better not cum before me.”

Her tongue picked up the pace and she opened her throat to take me deep and her eyes pleaded with me to fill her with my seed. I came hard down her throat and she licked the head clean before putting her hands back on her heels as she pushed down into the floor and her eyes rolled back and she came. I held her shoulder to steady her and then let her lay on her side as she was worn out from the intensity of the last ten minutes. She went to remove the vibrator and I smacked her hand. She laid on her side with it humming in her cunt.

She rolled onto her back and spread her legs. “That was intense. Can we go to the Anne Frank Museum and the Van Gogh Museum while we’re here?”

She was naked on the floor with a vibrator in her pussy. She was giving me a clear view as her hands rested on her chest still heaving from her heavy breathing and she wanted to talk about sightseeing. I wanted to laugh but wanted to fuck her as well. “Sure we can.”

“The Rijksmuseum has many great pieces of art. If we’re staying tomorrow maybe we can see that as well?”

“What about smoking pot and visiting the red light district?”

“We can do that at night after the museums close if that’s alright with you.”

“No panties in the museums.”

“Yes, Sir. I don’t feel bothered at all with no bra on. I kind of like it.”

“Don’t stop shaving under your arms and your pussy lips. I don’t want you going all European woman on me.”

“I won’t. I like the smoothness of my legs and they both lead to your favorite place.”

“Good girl. Do you want to cum for me again with your toy or do you want my hard cock in you?”

“Either would be great.”

“Lube up the toy and put it in your ass. I’ll fuck your pussy.”

She did as she was told and came five times before I filled her again. I think she was having second thoughts about Anne Frank’s house as I smacked her ass and told her to get moving. We stopped by to learn about Anne Frank and the life she lived in hiding as a Jewish girl in Amsterdam during WWII. Her diary that she kept while in hiding is world famous.

The Van Gogh museum was interesting but Tiffany had more of an interest than I did. I’d stop and look at the paintings that I liked. She looked at all of them and did a private tour with one of the staff. I liked the skeleton with Burning Cigarette, and the Wheat Field. It was interesting to see how many self portraits he had done. I was at a cafe sipping a cup of tea and talking to a woman I’d met when Tiffany finished her tour and caught up with me.

“Hi Brad, sorry I took so long.”

“Not a problem. I can do the whole Louvre in three hours. I was just talking to Emmy about the Van Gogh museum and she mentioned that there’s a house or museum where Rembrant lived and painted. It’s similar and something you may be interested in. Emmy this is Tiffany. Tiffany this is Emmy. We were just finishing some tea, and were talking about living in Amsterdam. Emmy had graduated and was looking for work as an architect remodeling houses or office buildings. She invited us to meet some of her friends and have a drink.”

Tiffany didn’t argue but just walked with us as we followed Emmy. We went over to the Waterhole and found a seat. There were pool tables and a stage for a band. The place was big and we ordered some beers. We’d pulled a few tables together and Emmy’s friends started to come in as work let out. We were introduced and Tiffany was soon in conversation with one of the guys. They were all about my age or a couple years older and most had just graduated college. We ordered more beers and some food to share for the table.

Emmy looked over and said, “Daan looks interested in Tiffany. You don’t look concerned.”

“I’m not concerned. Are you interested in Daan? I thought you were interested in me.”