"Sugarbabies" / "Arrangements" Amateurs or Not?

[DirtyDeeds38]

Hate to ask, but not counting the drinks and room, what was the donation? And also, here's to you, for giving us all some hope of better days to come.

Drinks were about $55, hotel was a comp with my points with the Hilton, otherwise it would have been a $169 for that room. I gave her $250. I think she is seeking a true relationship more than being a true SB. And I'm done with that nonsense for the time being. This whole SB deal honestly is what I've been looking for, for a very long time. As stated in the other posts, it's full on addicting, so I have to monitor that aspect.

[HollywoodGuy]

As posted yesterday, I had four options for the night and went with the sure bet. 38 year old mother of two. We met in Charlotte for a drink. I arrived first. She was right on time and as soon as she walked in I knew it was game on. This woman was fucking hot. Unbelievably so. Every man in the bar, with woman or not stared and she walked up to me. She was in a mini skirt, that revealed her more then average cleavage, legs for days, toned, fit, light tan, blue eyes and seriously the prettiest most perfect face I've seen on a woman in a very long time. She was blonde and obviously Swedish mix of some type. The woman was fucking stunning, a true, "woman's woman" and I wondered if I could keep up.

We sat and she drank. At first I thought she might be slamming them back at a good pace to help her "get through" what she was doing, but then it became apparent she enjoyed a good drink. She was well spoken, educated, classy, just plain fucking a pleasure to be seen with and talk to.

We had about five rounds of drinks, while she was touching my arm and leg in a lady like way and we talked. This told me she was game. So I popped the question if she wanted to get a room and without hesitation, she approved. During the walk to the hotel, we stopped and made out, passionately, her pulling at me, grabbing my cock, etc. We about did not make it to the room and I'm not kidding. LOL. In the lobby, during check in, same thing. DFK, heavy petting, everyone staring at this beauty with me.

Long story short, it was a solid 4 hours of head board hammering in the room. Every time I came and thought I could not muster up another round, she was on her knees sucking me hard again and then telling me to fuck her. We fucked in every possible position. Finally I had to tell her I was spent, had nothing left. She than turned sensual and all loving and cuddly on me. I rubbed her head and held her until she fell asleep. In the morning, it was another two rounds, but honestly, I lacked energy from the short night's sleep, drinking and that "not so fresh" feeling you have after a night of drinks and fucking.

As she got up to et dressed I was in awe of her beauty. This was not just a hot sexy woman, but the type that I would call a classic beauty. Nothing fake, hidden, or otherwise bullshit about her. Every part of this woman's body, face, skin, eyes and hair was perfect. I wondered why me. LOL.

I got a slight sense, of the ole, "what did I do" in the morning. Maybe a second thought about just having hooked up for a payment. But she agreed to see me again.

With a wonderful night, I still think I am opting for the younger girls. Something about their inexperience and feeling like a mentor that is just too appealing to me to give that aspect up. So as amazing as this woman was, I'm going back to the younger girls. But it was a very nice change of pace with a woman who was a fucking WOMAN in every sense of the word.

Hate to ask, but not counting the drinks and room, what was the donation? And also, here's to you, for giving us all some hope of better days to come.

[DirtyDeeds38]

As posted yesterday, I had four options for the night and went with the sure bet. 38 year old mother of two. We met in Charlotte for a drink. I arrived first. She was right on time and as soon as she walked in I knew it was game on. This woman was fucking hot. Unbelievably so. Every man in the bar, with woman or not stared and she walked up to me. She was in a mini skirt, that revealed her more then average cleavage, legs for days, toned, fit, light tan, blue eyes and seriously the prettiest most perfect face I've seen on a woman in a very long time. She was blonde and obviously Swedish mix of some type. The woman was fucking stunning, a true, "woman's woman" and I wondered if I could keep up.

We sat and she drank. At first I thought she might be slamming them back at a good pace to help her "get through" what she was doing, but then it became apparent she enjoyed a good drink. She was well spoken, educated, classy, just plain fucking a pleasure to be seen with and talk to.

We had about five rounds of drinks, while she was touching my arm and leg in a lady like way and we talked. This told me she was game. So I popped the question if she wanted to get a room and without hesitation, she approved. During the walk to the hotel, we stopped and made out, passionately, her pulling at me, grabbing my cock, etc. We about did not make it to the room and I'm not kidding. LOL. In the lobby, during check in, same thing. DFK, heavy petting, everyone staring at this beauty with me.

Long story short, it was a solid 4 hours of head board hammering in the room. Every time I came and thought I could not muster up another round, she was on her knees sucking me hard again and then telling me to fuck her. We fucked in every possible position. Finally I had to tell her I was spent, had nothing left. She than turned sensual and all loving and cuddly on me. I rubbed her head and held her until she fell asleep. In the morning, it was another two rounds, but honestly, I lacked energy from the short night's sleep, drinking and that "not so fresh" feeling you have after a night of drinks and fucking.

As she got up to et dressed I was in awe of her beauty. This was not just a hot sexy woman, but the type that I would call a classic beauty. Nothing fake, hidden, or otherwise bullshit about her. Every part of this woman's body, face, skin, eyes and hair was perfect. I wondered why me. LOL.

I got a slight sense, of the ole, "what did I do" in the morning. Maybe a second thought about just having hooked up for a payment. But she agreed to see me again.

With a wonderful night, I still think I am opting for the younger girls. Something about their inexperience and feeling like a mentor that is just too appealing to me to give that aspect up. So as amazing as this woman was, I'm going back to the younger girls. But it was a very nice change of pace with a woman who was a fucking WOMAN in every sense of the word.

[JZLizard]

I have addressed this before in this space and it is so true. In fact, I would venture to guess that most if not all guys in the Sugar world (including escorts, AMPs, cheaters) are addicts. I know I am.

An addiction is a dependence on a particular activity that makes your life unmanageable. This dependence usually leads to loss of control over one's life, and loss of family, loved ones, money, and sometimes jobs and ultimately one's life. Run while you can. I find myself not getting satisfaction from SO sex anymore. Sex with strangers, particularly hot young girls who I never had before is alluring and impossible to beat. Your SO cannot compete with the highs of this activity, so we are setting them up for failure.

I cannot wait until the next vaginal penetration, and I look at these girls as sex objects to be used for my enjoyment. Relationship? Not really. It's fun to have dinner and drinks, to squire them around to shock the housewives in public imagining their husbands doing the same thing. And to see the gleam of envy in the eyes of older men wishing they too had a size 2 hottie on their arm, and in their bed. Or you see that knowing glance from guys who are also in this world. " Good job Bro, you did well " I know they are thinking.

Why am I bringing this up? JL did, not me Haha. Thanks a lot brother. So I continue to search for that elusive "cheap" baby who can satisfy my needs, to feed the beast within me. To be the receptacle for my desires, and semen.

I believe that with enough practice, addictions can be manageable. When I was married, there was a period of about 3 years where I snuck out of the house 5 nights a week to go bar hopping and philandering. I was working from home so I had a lot of schedule flexibility, I would come in the house at 6 am many mornings, timing it perfectly before my ex woke up to go to work, yet never got caught cheating, not even once. Countless romps, countless beers consumed, countless hours spent in bars chasing multiple prospects at once and lining them up, giving each one the chance to satisfy my craving but only when I said when. Fucking them in my car if I couldn't find a place, or a hotel, or their place, wherever I could.

Unbelievably addictive. I became REALLY. FUCKING. GOOD at it. I had it down a science. This was back in the days before people used the Web to hook up, so nightclubs and bars were a pussy smorgasbord in those days in any large city.

In the end, despite never having being caught, it still cost me my marriage, a division of assets (OUCH! And a long period of time where I returned to exclusive civy dating, yet simultaneously realized what I had sacrificed in the process. How did the marriage end if I never got caught? Well because it changes who you are as a person, it affects your interpersonal relationships with others in ways you'll never see until it's too late. Karma is real.

Ultimately in reflection I realized where I went wrong. I lost control of my addiction. If you cannot summon the discipline to make yourself stop, it tells you all you need to know. It's just like the brakes have failed in your car. There will come a time when you need to slow the vehicle down quickly, and while that may not happen for some time, it's inevitable if you drive long enough. If the brakes don't do their job, you're fucked. It's the same with any type of addiction. If you cannot hit the brakes and stop the vehicle when you need to, you may not crash tomorrow but you will eventually.

So now, while I still think men were not designed to be monogamous, and I'm not pretending to stop all forms of cheating, I do "test my brakes" every now and then to be sure I can stop when I need to.

[FredMoore]

I have addressed this before in this space and it is so true. In fact, I would venture to guess that most if not all guys in the Sugar world (including escorts, AMPs, cheaters) are addicts. I know I am.

An addiction is a dependence on a particular activity that makes your life unmanageable. This dependence usually leads to loss of control over one's life, and loss of family, loved ones, money, and sometimes jobs and ultimately one's life. Run while you can. I find myself not getting satisfaction from SO sex anymore. Sex with strangers, particularly hot young girls who I never had before is alluring and impossible to beat. Your SO cannot compete with the highs of this activity, so we are setting them up for failure.

I cannot wait until the next vaginal penetration, and I look at these girls as sex objects to be used for my enjoyment. Relationship? Not really. It's fun to have dinner and drinks, to squire them around to shock the housewives in public imagining their husbands doing the same thing. And to see the gleam of envy in the eyes of older men wishing they too had a size 2 hottie on their arm, and in their bed. Or you see that knowing glance from guys who are also in this world. " Good job Bro, you did well " I know they are thinking.

Why am I bringing this up? JL did, not me Haha. Thanks a lot brother. So I continue to search for that elusive "cheap" baby who can satisfy my needs, to feed the beast within me. To be the receptacle for my desires, and semen.

[Rouleur]

I have seriously considered moving there. So many transient girls and college girls and of course hot girls, entertainers, etc. I went to a fetish party there once. It's every month and this girl who was a trapeze artist showed up out of curiosity, I snatched her up fast, played with her for an hour till she squirted on me a few times and then she bolted out the door. No goodbye, nothing. LOL.

Just a small example of "Vegas" I had a 18 year old Girl from Alabama, visiting Vegas with fellow High School Graduates, approach me near a Trader Joe's asking if I would purchase some adult beverages for her group. I had no doubt that she was selected to approach me, and whoever else, as she was like a young colt with long long legs that led to a tight ass and exposed stomach that wasn't overly cut but not soft either. Very perky breasts that basically said Hello to anyone in front of her. Beautiful smile and confident blue eyes that knew she was a hot young woman in a nasty nasty town.

I engaged in playful banter with her as I entered the store but made it clear I was not going to be the middle man for her group's Alcohol blast that night. She pouted in a way that said she wasn't really upset and I lost track of her as she went on to find another provider. A few minutes later, while I was staring at the fruit and thinking about the young ripe piece that had been so close to me moments before, the Girl showed up at my side again and said " I really like White Russians and, if later you buy me one, you might get lucky" with that she handed me a napkin from the Resort she and her group were staying at with her phone number on it. Without waiting for my reaction she turned around and sort of did that type of walk that kids do when they are really happy, sort of walking on the front of their feet with the heels barely touching the ground.

Guys, I am proudly very realistic about my looks and what I have to offer visually to women. I mean to say I am the most average looking late middle aged man you can imagine. I'm 56, grey hair, and a bit tall, 6'4" nowadays. I'm not currently in shape and no one would confuse me for one of the many retired pro athletes that live in this city. I was sure that the number was some kind of prank or set up for something really embarrassing. I had no idea that number was going to lead me to 48 hours of laughter, fun and sex with a girl I never imagined would be interested in spending time with me, much less ask me to let her drink my cum when we woke up together two mornings in a row.

I'm not very good at describing details so I'll save all of you from the misery. However the short answer to the question "why the hell me? 1. She was on her first trip away from her Parent's and Boyfriend. 2. She had been with her Girlfriend's father once when she was 17 and he "rocked her world, made her feel good" She was looking for another older Man to please her. And 3. She honestly wanted to have a "what happens in Vegas stays in Vegas" experience that she could look back on when she returned to Alabama. I just happened to be the lucky Man who won her prize.

[ThaiGringo]

I've been exploring and considering the SD / SB arrangement. What kind of budget is a minimum to play? This may be out of my league, but I sure hope not! If anyone can direct me to info, it would be much appreciated!

[HollywoodGuy]

I am, perhaps, one of those Men who could easily fall down the Sugar Hole and struggle to return to any sense of normal relationship. I'm divorced, financially comfortable where I don't have a work schedule to keep me preoccupied, kids are with the Ex, and I've had a vasectomy. LOL Oh, by the way, Las Vegas is my playground and the playground is in my back yard. There are so many SB's here in Vegas and I seem determined to meet all of them.

I have seriously considered moving there. So many transient girls and college girls and of course hot girls, entertainers, etc. I went to a fetish party there once. It's every month and this girl who was a trapeze artist showed up out of curiosity, I snatched her up fast, played with her for an hour till she squirted on me a few times and then she bolted out the door. No goodbye, nothing. LOL.

[HollywoodGuy]

Have you gotten checked out for hernia? Quite common in athletes over 40 and pain can be in lower abs or nuts or both or neither.

And if I lived in L. A. and could afford to be a full time SD, I'm not sure I would have a regular GF at all (although in my case I'm not sure I would be happier that way). Sex isn't that exciting with the same person over and over but a relationship can be satisfying in ways that makes up for lack of variety, especially when you get an occasional vacation to sow the wild oats.

I already had the hernia surgery about 2 years ago almost. I just have to release every 3 days max and I rarely go that long. I miss at most 8 days a month.

[John G Smith]

Good job but don't close your eyes on your SO either, you don't know. Those BFs also did not know!

Haha exactly. Actually just the other day my SO was telling me about how there are all these weird personal ads on CL. I played dumb of course but she could have very well read my Ad, LOL. She's not that good at being covert or covering her tracks, but still she very well could be meeting one of those guys.

[Rouleur]

I knew I was in trouble at the end of my most recent SB season when I met an unforgettable 10. When my GF returned from her travels, all I could think about is how could I find a way to put my GF back on that plane for a couple of weeks so I could continue my SB festival just a little bit longer.

When it was over, it took me a full month to fully recover, to remind myself why I was in this relationship in the first place, and to pull myself together / snap out of "the zone" and start enjoying the companionship I get out of my relationship again.

The bowl is extremely addictive, and will ruin your life if you allow it to. It's just like gambling, alcohol, drugs, sex, etc. In the sense that if done to excess and without a control factor, it will leave you penniless and without anyone in your life that really cares about you. I'm actually lucky that I have something of an automatic control factor that forces me to stop after a fixed period of time and resume my normal life. I suspect most folks have something similar (I. E. a wife that gets suspicious and limits activities, or kids to raise etc). If you don't have something like this to help you stop for extended periods of time, I would suggest just quitting cold turkey for at least 1-2 months, going dark and shutting down accounts, discontinuing existing contacts etc. Then start back up when you feel you have a handle on it.

You'd be surprised how many of those SBs are still there and available when you return. This past season I reconnected with a number of girls I had talked to the year before but never met, and yep you guessed it they are still interested. As others have said here, there is a constant flow of them, they aren't going away. Then if you start feeling a sense of addiction, go dark again, wait a month or two, and just keep doing it until your mind is accustomed to the start / stop cycle.

I've been meaning to write a little bit on the subject of holding our lives / marriages / jobs, etc. Whatever together while playing in the bowl. Recently I saw a TV show discuss a website called "RentAGent" where these cougars could hire stud-muffin GQ type guys for dates, or to clean their house shirtless or whatever (but no sex supposedly or the dude is fired). Sort of like an SB cub site for cougars. One of the more insightful comments was from a woman who said that the women who use this site need to be careful, because once they start surrounding themselves with these "perfect" men, they are setting a new standard for companionship for themselves that is unachievable in real dating, thus they are basically excluding themselves from ever finding someone who will truly make them happy.

It's a similar thing with the sugar bowl. Have fun and get your dick wet in some nice young pussy but jump back to reality every now and then to take care of life, or as the more trite saying goes play the sugar bowl and don't let the bowl play you.

I am, perhaps, one of those Men who could easily fall down the Sugar Hole and struggle to return to any sense of normal relationship. I'm divorced, financially comfortable where I don't have a work schedule to keep me preoccupied, kids are with the Ex, and I've had a vasectomy. LOL Oh, by the way, Las Vegas is my playground and the playground is in my back yard. There are so many SB's here in Vegas and I seem determined to meet all of them.

[JZLizard]

The longest I can go is about 3 days without sex before I get a very bad pain in the lower abdomen. No SO and jerking off is not an option. Too empty.

Have you gotten checked out for hernia? Quite common in athletes over 40 and pain can be in lower abs or nuts or both or neither.

And if I lived in L. A. and could afford to be a full time SD, I'm not sure I would have a regular GF at all (although in my case I'm not sure I would be happier that way). Sex isn't that exciting with the same person over and over but a relationship can be satisfying in ways that makes up for lack of variety, especially when you get an occasional vacation to sow the wild oats.

[Brian139]

Honestly I don't feel as bad cheating on my SO now that I'm seeing all these girls cheating on their boyfriends, LOL.

Good job but don't close your eyes on your SO either, you don't know. Those BFs also did not know!

[HollywoodGuy]

I knew I was in trouble at the end of my most recent SB season when I met an unforgettable 10. When my GF returned from her travels, all I could think about is how could I find a way to put my GF back on that plane for a couple of weeks so I could continue my SB festival just a little bit longer.

When it was over, it took me a full month to fully recover, to remind myself why I was in this relationship in the first place, and to pull myself together / snap out of "the zone" and start enjoying the companionship I get out of my relationship again.

The bowl is extremely addictive, and will ruin your life if you allow it to. It's just like gambling, alcohol, drugs, sex, etc. In the sense that if done to excess and without a control factor, it will leave you penniless and without anyone in your life that really cares about you. I'm actually lucky that I have something of an automatic control factor that forces me to stop after a fixed period of time and resume my normal life. I suspect most folks have something similar (I. E. a wife that gets suspicious and limits activities, or kids to raise etc). If you don't have something like this to help you stop for extended periods of time, I would suggest just quitting cold turkey for at least 1-2 months, going dark and shutting down accounts, discontinuing existing contacts etc. Then start back up when you feel you have a handle on it.

You'd be surprised how many of those SBs are still there and available when you return. This past season I reconnected with a number of girls I had talked to the year before but never met, and yep you guessed it they are still interested. As others have said here, there is a constant flow of them, they aren't going away. Then if you start feeling a sense of addiction, go dark again, wait a month or two, and just keep doing it until your mind is accustomed to the start / stop cycle.

I've been meaning to write a little bit on the subject of holding our lives / marriages / jobs, etc. Whatever together while playing in the bowl. Recently I saw a TV show discuss a website called "RentAGent" where these cougars could hire stud-muffin GQ type guys for dates, or to clean their house shirtless or whatever (but no sex supposedly or the dude is fired). Sort of like an SB cub site for cougars. One of the more insightful comments was from a woman who said that the women who use this site need to be careful, because once they start surrounding themselves with these "perfect" men, they are setting a new standard for companionship for themselves that is unachievable in real dating, thus they are basically excluding themselves from ever finding someone who will truly make them happy.

It's a similar thing with the sugar bowl. Have fun and get your dick wet in some nice young pussy but jump back to reality every now and then to take care of life, or as the more trite saying goes play the sugar bowl and don't let the bowl play you.

The longest I can go is about 3 days without sex before I get a very bad pain in the lower abdomen. No SO and jerking off is not an option. Too empty.

[JZLizard]

As the title says, I'm an idiot. The bowl is consuming way too much of my time, energy, and attention. Its affecting everything I do. But I can't stop.

I knew I was in trouble at the end of my most recent SB season when I met an unforgettable 10. When my GF returned from her travels, all I could think about is how could I find a way to put my GF back on that plane for a couple of weeks so I could continue my SB festival just a little bit longer.

When it was over, it took me a full month to fully recover, to remind myself why I was in this relationship in the first place, and to pull myself together / snap out of "the zone" and start enjoying the companionship I get out of my relationship again.

The bowl is extremely addictive, and will ruin your life if you allow it to. It's just like gambling, alcohol, drugs, sex, etc. In the sense that if done to excess and without a control factor, it will leave you penniless and without anyone in your life that really cares about you. I'm actually lucky that I have something of an automatic control factor that forces me to stop after a fixed period of time and resume my normal life. I suspect most folks have something similar (I. E. a wife that gets suspicious and limits activities, or kids to raise etc). If you don't have something like this to help you stop for extended periods of time, I would suggest just quitting cold turkey for at least 1-2 months, going dark and shutting down accounts, discontinuing existing contacts etc. Then start back up when you feel you have a handle on it.

You'd be surprised how many of those SBs are still there and available when you return. This past season I reconnected with a number of girls I had talked to the year before but never met, and yep you guessed it they are still interested. As others have said here, there is a constant flow of them, they aren't going away. Then if you start feeling a sense of addiction, go dark again, wait a month or two, and just keep doing it until your mind is accustomed to the start / stop cycle.

I've been meaning to write a little bit on the subject of holding our lives / marriages / jobs, etc. Whatever together while playing in the bowl. Recently I saw a TV show discuss a website called "RentAGent" where these cougars could hire stud-muffin GQ type guys for dates, or to clean their house shirtless or whatever (but no sex supposedly or the dude is fired). Sort of like an SB cub site for cougars. One of the more insightful comments was from a woman who said that the women who use this site need to be careful, because once they start surrounding themselves with these "perfect" men, they are setting a new standard for companionship for themselves that is unachievable in real dating, thus they are basically excluding themselves from ever finding someone who will truly make them happy.

It's a similar thing with the sugar bowl. Have fun and get your dick wet in some nice young pussy but jump back to reality every now and then to take care of life, or as the more trite saying goes play the sugar bowl and don't let the bowl play you.