SB Fashion

Over the (omg, has it really been that long?) four years since I first entered the sugar world, I've had to pick up some tricks in order to stay on top of my game. I realize looking back over this blog that a lot of my posts are about what an SD should and shouldn't do, so I've decided to start speaking to my sisters in sugar.

So, we're starting with clothing. I'm no fashionista, but I do love and respect clothes and the power they have.

As SBs, our goal is to attract men. We want them to be thinking about us naked, thinking about how much fun they could be having with us. However, we don't want to broadcast that to the rest of the world.

My SB 'uniform' of sorts is a J Crew v-neck cashmere sweater, dark wash jeans, and pointy-toed kitten heels. Heels are a must, for the sound they make on the floor and the general polish they give to a look. I'm tall, so I stick with kitten heels so as not to be intimidating.

If this isn't a first meeting, then the point of the outfit should be that it is sexy, but not overly so, and easy to take off while still looking sexy. Lots of layers or buttons and too tight jeans don't come off in a sexy way. I test an outfit by watching myself take it off in the mirror to see if I look ridiculous. A thin sweater is ideal.

I have in the past been a bit more 'business casual,' depending on what the SD needed, as far as discretion goes. In those cases I lean towards a nice shell and cardigan with black or gray dress pants. J Crew, Ann Taylor, Banana Republic are all good.

Accessories should be kept to a minimum. I have a pretty big bag that I like. It's nice to have room for a pair of flip flops for the walk home or other little things.

Also, a word on girl style versus guy style. That cute shirt dress, those ankle boots? That's girl style. A v-neck tee, tight jeans? That's guy style. An SB needs to dress for guy style. This means low cut, accentuates the waist, flattering clothes. Girl style is trendy and often not very figure-flattering. Save that for going to school or shopping. Guys just don't get leggings or chunky necklaces, even if they are the hot new thing!

Hotels do's and don'ts

Hotels become a routine with certain SB/SD arrangements. I've stayed in my fair share of 5-star hotels, but I did my best not to lose my sense of awe at the general opulence and sparkle that they all seem to have. I did however hide my awe as best I could.

For an SB, staying under the radar is key. I often reserved a room just for the day rate, which is a dead giveaway that something unusual is going down for the staff. I've gotten some amused looks and winks, as well as some glares.

Staying under the radar reduces the glares, I've found. I always arrive before my SD and simply text him the room number. This prevents awkwardness at the check-in desk, or at least minimizes it.

Always, and I mean always, put the 'Do Not Disturb' sign on the door, especially if you do the day-rate. The middle of the day is when the rooms are all being cleaned, and those cleaning ladies have keys. It's not fun to be walked in on, or have to get up in the middle of getting down to shoo them away. And I've had both happen to me!

Another tip to to dress conservatively. If you're getting there before your SD then you'll have plenty of time to change or take off layers, but this helps prevent the glares.

Finally, calling to make the reservation can be awkward, but doing it online usually means that you can't get a day-rate and you'll probably pay more. I really like Hilton. There are a lot of them in any big city, and often if your first choice doesn't have a day-rate room available the person on the phone will offer you another hotel nearby, at a slight discount for the inconvenience, of course!

Where's the Line?

I mentioned last week that I'm not a fan of being public with my sd/sb relationships. But where exactly is the line? Clearly I want to spend some time in public with an SD, especially while he's just a potential.

I love going out to nice restaurants. One of my favorite places to eat is at the Four Seasons. And, obviously, this is always done with an SD.

I think the line gets drawn when people around us know that we're sexually involved.

For a while I thought that outside of my city, or even outside of my country, I wouldn't care. That's been put to the test and now I can officially say that it doesn't matter what continent, I don't like when random people walking by or sitting next to me know that I'm fucking a guy twice my age.

So, how do you keep people from guessing? Keep the conversation away from anything related to sex, and even if it's our first time meeting pretend like we know each other a little. No physical contact (hand on leg, holding hands) should occur.

There are lots of SBs out there who would be happy to have an SD parade them around town. I'm not one of them, so if that's what a potential wants I have to wish him the best and move on. Oh well!

Flying High!!

I love flying.

I have always always loved flying.

And so... I love flying to see SDs. Obviously!

Pros: flying!!!, Nearly always Business Class/First Class, I'm flying, peanuts, flying, the views from up high, getting to fly, takeoff, flying, landing, I'm flying, turbulence, frequent flying miles, pretzels, Canada Dry.... and flying!

Cons: um, none.

However, I don't fly to meet SDs for a first meeting.

Just fyi.

Private Lives, Public Consequences?

I'm facing a dilemma.

Mr M is divorced. He has two other friends who have SBs, and as I said before he has had a couple of SBs of his own in the past couple of years.

I'm far more used to married SDs. In fact, with only one exception, every potential I've ever meet even just for a quick coffee has been married.

I realize now that this wasn't just a coincidence.

Married guys value their privacy. They have far more at risk than I do. Their family lives and even careers could be ruined by a run-in with someone they know while with their SB. This means that those sorts of arrangements, besides an occasional meal out, take place completely in private.

That is not Mr M's style.

He wants a girl to flaunt. He wants to go shopping and to the theatre. And while we're there he wants to make it clear to everyone that we are sexually involved.

That is not my style.

Let me be clear here, I am not ashamed, embarrassed, or otherwise mortified by being an SB. When I am alone with my thoughts I am not disturbed at all by being an SB, in fact I really enjoy looking back on my experiences so far.

I don't have a problem being with an SD in public, I have a problem with an SD groping me and saying inappropriate things to me in public. I guess I was only meant for married SDs!

So, Mr M and I will be having a little chat next weekend when I fly to visit him. We will not be going shopping at Victoria's Secret together. We will not be going to ballet. We will be staying at his beautiful condo so I can cook a wonderful dinner and cuddle on the couch to watch a movie. Unless he learns to keep his hands to himself in public, this is how it will be.

In the mean time...

Although C is clearly my preference, I have met with another potential and will probably keep him around for a while. Mr M is perfectly nice, almost too nice.

I'll explain by telling you about our first meeting. He was in town last week, so I made some time to see him after work one day. We met at the bar of the posh hotel he was staying in. He hugged me right off, and was in general a bit more 'touchy-feely' than I like to be in public. That rule goes for boyfriends and SDs alike. I'm not a huge fan of lots of arm touching or hand holding, and kissing is absolutely verboten. If I'm in public with an SD, the general population should not automatically wonder if we're fucking each other.

He has had four previous arrangements over the past ten years or so. To me that means that he probably has a very specific idea of what his SB should be, and what he expects from the arrangement. That can be great - if it matches with what I'm looking for.

I think in general he is a match, except for his desired level of privacy. Despite not being ashamed or guilty or anything like that about being an SB, I don't like for the general public to know about it. Mr M doesn't seem to care if the people sitting next to us at a restaurant figure it out or not.... actually, I think he might want them to figure it out. With the age difference hovering right around 30+ years, I'm really uncomfortable with that.

But, he's a huge sweetheart. He brought me chocolates, and insisted on calling a car for me (not a cab, a chauffeured car). So, one of these weekends soon I will be making the short flight to see him on his home turf. I'm looking forward to it and not at the same time. C is still my priority, but Mr M is a good alternative should C end up falling through, as so many great potentials do!

A Little More About C

My favorite current potential will be flying into town in a couple of weeks! I'm really excited to meet him finally and see if we work well together. He's coming out here for business, so I feel a lot less pressure. I've had a couple of potentials in the past fly in just to see me, so it's nice that he has something else to occupy him during the day.

I'm very excited about this potential. He's quite attractive and when we've spoken on the phone I've felt very comfortable with him. He's intelligent and we have a lot of similar interests. It's always nice to find someone I can have a conversation with about an article in the Wall Street Journal or New York Times.

We've already worked out the general details of how our arrangement would work, right down to which flights are best. I would fly out to visit him every other weekend Friday night after my internship, then take the red-eye back home Sunday night/Monday morning. He will be doing business in my city a bit more often, and will probably visit once a month.

He's done this before, with another college student. She also had to fly in to see him. He's a busy guy, so he assured me that when I visit him I will probably spend a lot of the time alone in his house while he is working. Perfect for me to be able to keep up on schoolwork.

All in all, I really hope when we meet everything is as perfect as it seems on paper!

From My Diary Part 2

Con't...

'J was just walking up to the entrance of the bar as I came from the other direction. We had an awkward moment of just staring at each other, and then we introduced ourselves, shaking hands. He's tall, fit, and far more handsome than I thought from his photo!

The bar was elegant and dark. One side was a traditional bar, but most of the room was plush chairs around tables and leather couches around a grand fireplace. He ordered a beer and I got an iced tea. He asked me a couple of questions about school, and I asked him about the trip he was leaving for later that afternoon.

He started talking about his job in finance and that carried the conversation until it was almost time to leave. He explained to me how he went from rich to uber-rich by making a risky investment about five years ago. It was science related, and he glossed over the technical aspects of it. I felt a bit insulted because he seemed to assume that I wouldn't understand even basic scientific principles. We can't all go to an Ivy League school!

We finally got to the real subject.

He said he only wants one girl. He's never done this before, and he wants me to be exclusive. I made sure to say that I don't need the money, that it's more about fun and excitement for me. He wants to 'help' someone, so I played up my tuition costs.

Once we decided to leave it got awkward again. We talked about how nice the hotel is on the way out and in the elevator.

I'm really looking forward to seeing him again!'

...
So there you have it! J was my second SD experience, after M. I knew a bit more, but still honestly had no clue what I was doing. Hopefully that just came off as endearing and not stupid to the guys!

From My Diary

I've decided to do a direct post from my diary of the first time I met my favorite SD, J.

'So I met J yesterday, but before I talk about him I have to talk about the hotel where we met.

A doorman pushed the revolving door for me so I wouldn't even have to touch it! There was a small entryway, very dark, classy, where I walked up to the front desk. They directed me to a bank of elevators.

A bellman led me to the elevators, pushed the button for me, an said 'Have a good day' as the doors opened.

I stepped out into a grand hallway, which I followed to the Lobby. I was so nervous that everything seemed strange, blurry, distant. The lobby was a huge room 5-6 stories up, with an alcove tucked up a floor over the whole room with a cellist playing. A cellist! In the middle of the day! I'm still in awe of everything I saw.

J was no where to be seen, so I ducked into the ladies room. Even the towels looked luxurious. I texted him quickly, and he said he was only a minute away. I composed myself and walked out of the bathroom.'

I'll post more tomorrow! Just wanted to give a sense of what that moment right before feels like.

My First Time Having Sex for Money

I mentioned my first meeting before here and here.

I did end up seeing M again, quite soon after that meeting. Luckily I didn't scare him away with my inexperience and inebriation!

We met at the same bar again, and each had a drink. He had been to the doctor's office earlier in the day, so we talked about his sports injury. I originally thought he would have to cancel because he had been through minor surgery in the office that day, but he was insistent that we meet anyway.

Almost the second we stepped through the door of his condo we were at it. We had the quick mumbled convo about birth control (pill and condoms!) and before I knew it I was naked, laying across his bed!

Please keep in mind how terribly, terribly inexperienced I was at this point in my life! This is certainly not what I consider an 'ideal' meeting!

He went down on me, something I had never before experienced (ahem, college guys suck at sex). I didn't know what to do, and honestly was a bit uncomfortable. When it was my turn to reciprocate I was relieved.

M was average sized, nothing extraordinary, but certainly not disappointing. The sex was average as well, lasting perhaps 5 minutes, in missionary.

We talked for a while after. I was a bit inebriated (again). He asked if I'd ever thought about getting implants. I responded that if they ever find a way to make implants pain-free I'll be first in line! Until then, there's no way I'd ever agree to unnecessary pain. I have very low pain tolerance.

We got dressed, and he walked me out. In the elevator he handed me an envelope, and said he hoped it was enough. We hadn't discussed money at all beforehand. He joked that it was probably the easiest money I'd ever make, and I nervously laughed with him.

Certainly not a terrible first time, however I learned a lot from it (when I sobered up).

Funny note: When I got home 20 minutes later I ran into a friend on my way into my building. She grabbed me and made me go out for a snack with her and a bunch a friends. The whole time all I could think was 'Please dear god don't let them figure out that I'm tipsy... or notice the economy pack of condoms in my bag!' I got away with it somehow!

My First Meeting P2

I am sorry for not continuing this post earlier. I've lost my journal from that year, and I wanted to try to remember more details. Alas, it seems to be truly gone (whaaa!), so here goes!

When he returned we sat and talked a bit longer, and then he suggested we head out. At this point I will admit I had drank (drunk?) half the glass of wine and two cosmos. Remember I was only a little froshie and the whole drinking thing was new to me, so I was definitely tipsy.

We began to walk out of the bar and down the street. At first we were heading towards the subway, but then we weren't. I didn't say anything. Next thing I knew he was holding open the door to a gorgeous condo high-rise. We went upstairs, past the two smiling doormen. His one-bedroom condo was beautiful, clearly professionally decorated.

He excused himself to the bathroom, so I sneaked a peak of the view out the window. Gorgeous. When he came out we sat on the couch talking for a bit.

Then he asked me if I wanted to go to the bedroom. I blushed horribly. I apologized and said I wasn't sure why I had come back to his place with him because I didn't intend to have sex on the first meeting. He said that was fine, then asked if he could have a blowjob.

Embarrassing, but true, I really was inexperienced with the BJ, so I said no. He said that was fine, again, and offered me a ride home.

We took a taxi to one of his properties a couple of blocks away where he kept his car. The gate's lock was iced, so after struggling with it for a couple of minutes we walked from the front of the brownstone around the block to the alley. He had a brand-new Lexus.

He drove me home, and kissed me when he dropped me off. Nearly the whole drive there he had been on the phone with his wife, directing her on packing their vacation home.

And that was my very first meeting with a real live sugar daddy!

In Honor of the Holiday...

We shall be discussing drinking and SDs. How much, when, and where!

I see nothing wrong with drinking with an SD. Infact, more than half of my first meetings have been at bars or similar places. A glass of wine or a Cosmo seems to be the best way to go.

My very first meeting I got a little too tipsy. I wasn't drunk, but I also wasn't fully aware of what was going on. I said things I shouldn't have, and I ended up back at his place and in a very awkward and dangerous situation. Thank god he turned out to be a good guy!

So drinking is ok, but drinking St Patties Day style is not!

Wine I think is preferable to any other drink simply because it is seen as feminine, and if he (and you!) know anything about wine it's a good topic. If you don't know anything about wine, try to at least learn some basics, like what types or reds you like, or even what a red is!

Having a drink is a great way to relax, for you and for him! Plus it gives you something to do with your hands! I never know what to do with my hands!

Social Norms, etc

I fully realize that these sorts of arrangements are not viewed by the general public favorably. I've mentioned before that I do not tell anyone, friends or family, about what I do.

I do fear people I know finding out. I go to great lengths to avoid this.

The main thing is to protect my profile. The internet is a big and scary place, and bad things can happen very easily. I do not ever put face pictures on my profile. I have heard all sorts of statistics about how face pictures get more responses, but it simply isn't worth it to me. My father has referenced one of the sites (one I'm not on, thank god!) and friends have joked about sugar babies and daddies too often. I send face pictures once I've gotten an email or two from the guy. It's just discretionary. When I feel comfortable, you see my face.

Another thing I do is meet in places away from 'my' area of the city. I like to be comfortable in my surroundings on first meetings, but not too comfortable! I have been lucky enough to not have had any run-ins with people I know while with an SD.

I do like to be prepared though, and it seems the SDs are just as worried. Coming out of a hotel once with an SD he quickly pulled me aside and said his best friend and his wife lived in a condo just down the street. If he were to be spotted I was to act like I had asked for directions! In the future we avoided this by simply leaving the hotel at different times. I had to check out of the room anyway, so it just made sense.

Would it be better if I could tell someone? Sure! But I don't think any of my friends would approve, so I keep it to myself. I think it's a secret I will have to keep forever unfortunately.

I'm a safety kinda gal

Safety is huge for me. If I get a funny feeling about a guy, I cancel. I avoid risks, because meeting SDs is risky, just like any type of online dating.

One guy who I was talking to set off some major alarm bells when we were setting up our first meeting. He asked if I wanted to meet at his condo for a drink before dinner. I said I preferred to meet at the restaurant instead. He seemed cool about it at first.

Then he starts telling me about how he thinks it's great when a girl is confident enough to just go over to a guys place before meeting him. He said he thought it showed that she was cool and really interested in him.

I was stunned. Personally, I think that any girl who does that is an idiot just asking for trouble. Clearly he doesn't actually intend to make it to dinner when he's already got you in his condo drinking wine.

I ended up canceling on him. He eventually agreed to meet me at the restaurant, but I still wasn't comfortable after having had that conversation with him. Also, he lived very close to me. Even though it's a big city, it still made me a bit nervous!

Giving Craigslist a Shot

I mentioned earlier that I responded to a couple of craigslist postings, and was interested in one or two of the men. Well, one pulled a 'my ex and I got back together' just six hours before our first meeting was scheduled. The other could only meet during the day, so it took me a bit longer to set up a time to meet him.

Boy, am I glad we had that extra week to talk over email before I wasted my time on him!

Normally I am not big on talking about money or sex before we meet, but he asked so I told him what my allowance was with my previous SD. His email in response was hilarious!

'Wow. That's a whole other league.'

He then tells me that with his previous SB he gave her less than half what I asked for, and met up twice a week! It boils down to less that $200 each meeting!!

I quickly responded that I didn't think we were suitable, not because of the money but because my schedule does not allow me to meet up more than 3 or 4 times a month. And, of course, I wished him the best of luck.

Sometimes I am just amazed with how much men want for so little. I suppose he saw an SB as a sort of bulk-buy escort. Give her an allowance and maybe, just maybe, she won't notice that it's a total ripoff. Too bad for him I'm not lying when I say I'm a college student, and I can quickly figure out if he's worth it or not.

Oh, and I wasn't lying about not being able to meet twice a week. I would have had to turn him down even if the money would have been adequate.

My First Meeting P1

I was so nervous. The whole way there on the subway I had my ipod on really loud, trying not to think about what I was doing. I nearly didn't go. I called M earlier in the day and almost canceled. In the end we agreed to meet a little later than we originally planned.

As I walked up from the subway and down the street I nearly turned back around. What was I doing? Meeting a man nearly old enough to be my father, in a bar when I was only 19!

I was relieved when I made it to the bar, but only because it was so cold outside. Once I thawed out and took a look around I realized that I didn't see anyone who looked like the picture he'd used on his profile. I started to panic. What if he wasn't there? What if someone carded me? What if I knew someone in here?

Just as I was about to leave a man sitting alone at a table caught my eye and mouthed across the room 'CB?' I nodded and made my way over.

He wasn't the man from the photo, and he later explained that it was a picture of one of his friends. He was actually more attractive, and after the first couple of minutes I felt fairly relaxed with him.

I had no idea what I was doing. I hadn't planned in advance what I was willing to tell him and what i wasn't. We talked about our families, and I ended up saying more than I should have. I'm lucky it never came back to haunt me!

He had two homes, one here in the city and one down in Florida. His wife and kids were down in Florida, and they rarely came to our city. He was here a lot for business. He was in real estate in some fashion. I wonder now how he's doing. If he managed to escape the bubble popping and all that.

He ordered me a glass of wine as I had no idea what I wanted. When it came I drank only a little of it. I didn't want to get drunk. He took this to mean that I didn't like it, so he asked the waitress to take it back and get me a cosmo instead. I felt so embarrassed!

After we had been there nearly an hour he took a phone call from his wife. He stepped outside after the intial 'Hi Honey. Yes, still at the bar, watching the game.' I wondered if she could tell, but I didn't feel any guilt.

TBC...

Expectations for First Meetings

'Expectations' might not be quite the right word, but it's close. I have general ideas on how a first meeting should go. These are flexible and are simply guidelines, but in general they fit.

I know a lot of girls expect a gift of some sort on the first meeting, but I never have expected that, and I never have received that. What I do expect is for the man to pay for whatever drink/food I order. This has never been an issue, as I think it's understood. Also, I would say 75% of the time the man offers to pay for my cab ride home. I usually accept this, and it's always nice to have it offered.

First meetings should never be too long. I would say anything over an hour and a half is too long. One man said he only had time for a quick meeting, and then we ended up sitting in the bar for three hours. Too long!

Topics of conversation should be like any first date, although when we first meet in the bar/restaurant/whatever I never say 'So nice to meet you' or anything like that. I wouldn't want the people around us to think anything other than innocent things about what we are up to. I do talk a bit about my background, but I keep it vague. I'm always surprised when men give me very intimate details of their lives, when they've only just met me!

In general, I'm here to see if we have any chemistry. Don't try too hard, it backfires. I'm also making sure that you are who you said you were online. Most importantly, I'm doing a gut check. Do you freak me out? Do I get a bad vibe? Do I feel that I could spend time with you and enjoy it?

That's it!

Nailing it all Down

Talking about specifics of an arrangement is very tricky. I've dealt with everything from first emails outlining exactly how often they want to meet and what allowance they want to give, to never even discussing those things.

Personally, I prefer to wait until after we've had a first meeting to talk about specifics, through emails. This way we've already established that we both would like to go ahead with an arrangement, and can get the business out of the way.

Many guys want to talk about it during the first meeting, but this puts me off a bit for two reasons. First, we're in public, and god only knows who is listening in on what we are talking about. Secondly, it is awkward no matter how you look at it, and discussing it in person, especially if we disagree in anything, just makes it more awkward.

I've actually had one arrangement where we never discussed neither how often we would meet, nor what type of allowance he was willing to give. It worked out fine, but didn't last long as I think neither of us was happy with the situation.

The easiest thing for me is just putting it in my profile. I make it very clear in the text of my profile how often I want to meet a month, and both sites I'm on have a place to put 'desired allowance.' I hate that most men put 'negotiable.' This doesn't help me out at all! You must have a number in mind, just tell me!

First Meeting Nerves

I'm always nervous. Always.

The more that I want you to like me, the more nervous I'm going to be. If for instance you are really cute, or you seem like the perfect potential, I'm going to be more nervous than if you're a bit out of my target age range, or seem cheap.

But I'm still nervous.

The handful of first meetings I've had have mainly been at bars. They've ranged from a neighborhood bar where the guy said everyone knew his name (a bit creepy) to the bar at a 5 star hotel which had an elevator attendant. I've also had first meetings at coffee shops, restaurants, and one on the steps of a museum.

I have a couple of rules, as I've mentioned before, but I forgot to mention one that applies to first meetings.

I don't shave my legs.

Yeah, you heard me. I don't shave my legs. This helps me keep another one of my rules, not to sleep with a potential on the first meeting. This, of course, is waived in the cases where I've gone in knowing ahead of time that I was going to sleep with the man right away, but that's only been twice. It's probably a little silly, but it seems to do the trick.

I was tempted once, and was so glad that I had that to keep me from breaking my rule!!

The Rules

I'd like to think I'm a pretty laid back kind of girl, but even I have a couple of simple, basic, easy-to-follow rules that every guy must comply with if he wants to set up a first meeting.

1. I must see a picture of you.
This is important for my own personal safety, and simply for general peace of mind. I do not have friends that I can talk to about this aspect of my life, so when I'm going to meet a potential for the first time I save his photo and general information in a Word document on the desktop of my laptop. If anything goes wrong, the cops are going to find you!
I also hate the feeling of going into a restaurant or coffee shop or bar and not having any clue as to who I am meeting. One man told me he thought it would amuse him to watch me try to figure out who he was in a Starbucks at noon. Yeah, it might be fun for you, and in general I'm all for playing games, but let's keep those games confined to the bedroom!

2. I must have your phone number
Lots of guys 'block' their phone number when they first call me. Again, this is just a simple safety issue.

3. We meet in a public place
Safety safety safety. I'm just a safety kind of girl! In general this has been either a bar or a restaurant. Coffee shops are fine, but I always prefer to have the meeting be around an hour long to really see if we have any chemistry, and who wants to sit in a crowded starbucks for an hour? Not me!

4. We are not going back to yours quite yet (sometimes)
I've broken this rule twice, and both times (Mr D included) I did not regret it, and both times it was because they flew into town just to see me.
In general though I think it is better (for me and for the potential) not to have any expectations of that type so we can spend the time seeing if we have chemistry.

With most potentials I never even have to mention my rules. Most are gentlemen and provide me with everything I could want to feel safe and comfortable when I am with them. I have never been in a situation where I did not feel safe with a potential or with an SD, and for that I am beyond thankful!