"Sugarbabies" / "Arrangements" Amateurs or Not?

**Literal2** · 06-02-11 16:53

I think Golf is assembling pieces of the puzzle as to how and why some of these girls let us do what we do. Very interesting. Lots of good ideas here, inmo.

It doesn't work the same way for every girl, but the skilled utr monger needs more than one technique if he is going to harvest as much amateur quality pussy as he can.

**Coolhand2** · 06-02-11 14:46

CSB7 (New) - 23years old; 5'6. We had the usual back and forth emails on the SD site then switched to private email where the messages got more and more erotic. Then she started sending me several nude pictures of herself which really got my interest. Really tight body with enough curves so you had a cushion. Not curvaceous like CSB6 (who was like the women on Mad Men) but nice. Well I met her last night. I actually picked her up at her home. She lives with a girlfriend and the girlfriends mother. The 200 lb girlfriend comes out to tell me she'll be out in a minute. (I think that was to check me out.)

Out she comes wearing a neck to ankle one piece very tight dress that shows off her curves without going overboard. She is exactly like the pictures. After stopping to pick up some drinks, we proceed to the fucking chamber, where a good time was had by all. She was very sensual, wanted to please and was absolutely tireless. Oh to be 23 again. She had above average skills in all departments but I may be judging to harshly. The problem is she was following the two time super bowl quarterback (CSB6) and that is the hardest thing to do. She did a thing that had my balls and half my cock in her mouth which she teased with her tongue. That was unique. Afterward I took her home.

Now get this: it was a nice night and she invited me to sit with her on the swing on the porch. She even offered ice tea. I felt like I was 18 dropping my date off. I couldn't accept the offer because I was really pushing the time on my pass from the warden so I had to go. It made for a overall quite unique experience. Fucked like a minx (and a squirter) ; acted like a school girl. I will definitely see again.

**Coolhand2** · 06-02-11 14:39

CSB6. Saw CSB6 last Thursday. Certifiably a World Class Fuck. This time was just as good as the first. Sadly it may be my last. She said she was happy with the sugar but since our visits are spaced out so far she needs some sugar in between. This is not happening so I may have seen the last of CSB6.

CSB3. The 21yr old who broke off our contact for another guy contacted me again last week. She said the guy was tight with the sugar and made her ask for it. She said this made her feel bad. So after some back and forth (in which she said she needed rent money) we were supposed to meet. Turns out she wanted to go on several dates before giving up the pussy so she wouldn't feel like a s___. Actually her exact words were a "s___ slave." WTF! I'm over 60. What would I look like dating a 21 yr old? I want to fuck them, not date them. After a few more back and forth's I determined this was definitely more trouble then she was worth; wished her a nice life and moved on.

CSB7. She deserves a seperate post. See above.

In the mix. I have a 41 yr old. 5'6 massage therapist; a 38 yr old 5'4 nurse and a 28 year old. 5'2 women in the Navy. The 41 yr old says she was in a 12 year SD / SB relationship with a married man who moved to Florida It has not come up but I'm concerned that my sugar amount may not be enough. Neither have pictures on the sight but the 38 yr old sent me pics by private email. No nudes but the pictures show a nice looking, short haired brunette with very nice breasts. I spoken to the 38 yr old and plan on calling the 41 yr old today. I'm trying to set up a meeting with the Navy girl tomorrow. Her pics on the sight are nice and I have spoken to her on the phone. I'm planning on moving slow because a scheduling issue caused me to lose two others I was working on. I think that's it. Pussy is wonderful.

**Golfcart** · 06-02-11 12:55

I see Literal2 is at it again.

Originally Posted by Literal2 [View Original Post]

(edit delete) She's a senior in college, she says, and plans to get her MBA. Smart as hell. Why would this highly desirable female choose to let an old man fuck her and how could she possibly enjoy it so much? I'm not sure. Yes, I make nice gifts to her, but is that what gets pussy juice flowing? I think the answer has something to do with the safety of a sb / sd relationship from the point of view of the girl. She knows I'm never going to be part of her social group so she can just abandon herself to desire when she is with me. Maybe that's it, maybe its something else. (edit delete)

I have this theory. Every woman will turn a trick under the right circumstances. She will do it for the excitement of being desired by a strange man willing to pay her. But she has a disconnect of not seeing herself as being paid. She'll see it as showing appreciation to a friend who helps her out. She may see it as 'found money' there for the taking he would be giving someone anyway. Either way she is not in there being paid. This is not what is happening.

The guy's treatment of her and how the money is handled must conform to her sense of reality, not his, or he'll blow what he found. Few girls ever take the next step. It is a big one to a woman and few ever get over it. She'll be gone once she senses he has a different sense of reality, the instant he treats the money as payment which usually happens when he attempts to control her (or say the wrong thing). No joking. Seriously, no joking around.

With a woman what we say will get us into more trouble than what we do. Do not say anything about the money. Do not give her the money first. Do not even hand her the money. Not that there aren't other ways, I put a rubber band around it and put it in her handbag while on the elevator leaving as the door is closing, a good distraction, without saying a word. I cup my hand so nothing is seen.

The guy must treat her normally, like a regular person, not like a date even, like we would treat a guy friend of ours, a guy in our foursome, not make a big deal over her, not make a big deal over it, certainly not expect it, and she must have the security of being able to withdraw at any point without any entanglements, without getting caught should she change her mind or should she go through with it. She must be secure she can walk away with no consequences, no fear of discovery. With that security she'll turn a trick. That he may be an old fart is inconsequential unless it makes him safer to her. All that matters is how she is treated, and money magically appears.

Literal2 made a comment earlier about a poster who enjoyed learning all her personal details, her real name, etc. The poster was invading her space and Literal2 took him to task. Good. She will see that as a threat to her free will to withdraw with no fear of entanglement. It will kill the goose that lays the golden egg.

**Literal2** · 06-02-11 08:23

It was a dream. 22 years old, blond, cute, perfectly proportioned slim, not skinny body, her tits and ass small, firm and curvy. One small tatoo. She greets me at the door with dfk, pushes me back to the bed, hikes her skirt up, straddles my lap like a dancer. She presses against me with her crotch. She gives a big smile when I feel under her panties how warm and slippery she is. Three minutes in the room, how could she be so wet? She pulls her dress off over her head, and unbuttons my shirt. She kisses and licks my chest and belly as she slips to her knees between my legs. She unzips my jeans. She sucks on Mr Johnson for several minutes. She's sighing, I'm gasping. It just gets better from there.

She's a senior in college, she says, and plans to get her MBA. Smart as hell. Why would this highly desirable female choose to let an old man fuck her and how could she possibly enjoy it so much? I'm not sure. Yes, I make nice gifts to her, but is that what gets pussy juice flowing? I think the answer has something to do with the safety of a sb / sd relationship from the point of view of the girl. She knows I'm never going to be part of her social group so she can just abandon herself to desire when she is with me. Maybe thats it, maybe its something else.

Some girls, like sb16, are very mechanical and businesslike. I think she enjoys me fucking her but she wants it over with fast. She sent me an email this morning,"When can you see me again?" When we are done she runs back to her age group. I'll put her off for a while.

SB18 lingers with me as long as I let her, not clinging, just being sexual.

I wonder if in 2011 Sex Prison it would be possible for an old stallion to keep a herd of young fillies around indefinitely as an alternative to conventional life. Billionaires do it of course, but what about the rest of us? Doing the math, it would certainly be cheaper than a marriage or worse, serial marriages.

The fillies would come and go and at some point you'd have to check into a nursing home I guess. But maybe not. I read on a Mexico blog a few years ago about some old dude who took his RV down to Baja and lived on the beaches. He woke up dead one morning in his beach chair with multiple stab wounds. Maybe he was servicing the local young women and the young men decided they'd had enough. Not such a bad way to go, really.

**Literal2** · 05-31-11 15:58

Two of the strippers who finally agreed to come to my fucking chamber were so worked up before they got there that they were very good fucks indeed. The 22 year old mom squirted all over me cowgirl and finished, as I said, with the worlds best bbbjtcws. The early 30's fiance-stripper was so anxious and hot after I didn't visit her club for a few weeks after she turned me down that she pulled my waistband out and stuck her face and tongue into my pants in the VIP."Are you going to take your panties off for me, Jennifer?" I asked."YES!" she said. Then we met at a hotel about six times. This was not in Virginia. I never had any success at a sc in Virginia.

I'm trying to keep things alive with all the best sbs I've had over the past few months. I've put atf SB4 on the shelf but stay in touch with her and will go back to fuck her when I can but I really like her and worry about getting tangled up financially and otherwise. By the way, I posted a photo of her perfect ass a while ago and I look at it to remind me of her. Do any of you guys have acess to a more perfect ass than SB4? If so, show and tell, let's see what it looks like.

SB16 last week was an ok second fuck. She's 27 and flat but tight. She showed up wearing some kind of rubberized little black dress wrapped tight around her body and barely concealing her crotch. Very nice but she doesn't like foreplay, oral, titty play or anal. It's wham bam as I said and it's not enough for me.

SB11 was a good second fuck. When I asked if she liked doggie, she said,"I'll do it if you want." When asked if she liked cg, she said the same thing. She said,"What I really like is you on top of me." Well, it turns out she also loves getting her clit brushed rapidly by hand and deep fingering, but when I finally penetrated her she just locked her legs around my back, arched her neck and moaned like she was dying. Very satisfactory experience. She said she just wanted one sugardaddy and I was it. I told her I was the wrong guy for her.

SB18 is apparently coming back to the fucking chamber tomorrow. She makes me realize how a smart, sexy 22 year old girl can make a fool out of a senior citizen. I have to watch myself around her. She's the only real rival to SB4 for my affections. She is fair while sb4 is dark haired. SB4 has big boobs, sb18's are small and pretty. SB18's skin is tight all over and she does everything I ask with enthusiasm. Unbelievable.

SB3 is being a pest, emailing me all the time about getting together again. She made me wait for months. Now I'll make her wait for months, assuming I ever go back to her, which I may not.

**Magic Rat** · 05-31-11 13:20

I've had a couple regular stripper friends and the relationships were very similiar to the ones I've had with sugarbabies. As someone else said, it did take a lot of itc meeting, talking, dancing until they were comfortable with meeting outside. Plus both dancers were older than your typical stripper, one early 30's the other mid 30's. Both have their head on straight and are a lot of fun. Interesting thing though, IME the sex with the strippers has been a little more plain vanilla than with the sugarbabies, but that could be because my regular sugarbaby gigs have been with women in their early to mid 40's. I've had the wildest sex of my life with these type sugarbabies. Seems as if their sex drive is off the charts, plus they seem to get a lot nasier in their sexual preferences than the strippers I've known. Best of both worlds maybe? No complaints here for sure.

And BTW, I'll echo what others have said regarding Literal. I appreciate his posts and contributions. Never considered him a barn boss or whatever. It's just entertainment folks!

**Coolhand2** · 05-30-11 14:46

Originally Posted by Varoom [View Original Post]

No apology needed Lit2. It seems as though this little tif placed a bit of a damper on the info Lit2 was willing to share over the past week or so, almost in a concious effort to back off and not be the Barn Boss. But I think that most will agree with me, we appreciate and enjoy the way Lit2 has moderated, instructed, reported on your thrists, and overall conducted matters here in this thread. I for one feel that we are missing out on some reporting by Lit2 on his recent events with SB18. Oh and SB 11, or SB 4, etc, etc. In the words of Sgt Joe Friday (slightly altered);"Lets have the facts Lit2, just the facts." (and feel free to embellish the hell out of them for our reading pleasure). I for one appreciate Lit2 experience and efforts, both with the ladies and his willingness to share those experiences with the rest of us.

How do the rest of the contributors of this thread feel about this?

I for one started pursuing SB solely based on this thread that Lit2 started. Even though I have not had the success that he has had, I am appreciative of the advice, insight, and the inspiration that he has provided. As I've said before, he is the Gold Standard when it comes to SB's. I want him to keep the info coming. I always look forward to it. He has earned the right to be Barn Boss

**Literal2** · 05-30-11 08:11

Vroom: thanks, it's ok. In some weird way I feel protective towards the women I exploit, but enough said.

Golf: your stripper was 1 in a 100 I think. She's probably married with kids and normal life by now.

Mad: well, strippers do tend to be fit, at least the good ones do. Management weeds out the ugly ones. There are exceptions, of course. The sbs I've been seeing have all shown me photos before I meet them but several times the photos are a few years old and the girl is older or heavier. I have walked away from a couple of sbs. On average I think my sbs are at least as attractive as strippers though because they don't have the hardness a girl gets from taking off her clothes for strange men dozens of times every day. They don't make themselves up slutty either. In my experience, you always get a shock when you see a stripper outside in daylight.

**Madaboutmax** · 05-29-11 20:27

Originally Posted by Cantwinlosin [View Original Post]

I make it a standing rule to not involve myself with dancers. There's too many other amateurs out there that don't come with all the baggage.

Maybe this is why I am so interested in this thread. The idea of finding an amateur as good looking as a stripper, but without all of the drama is intriguing. So how would you guys rate the looks of some of your "amateur" SB's on the stripper scale?

**Golfcart** · 05-29-11 19:20

One of the best pieces I ever had was handed to me by a stripper. Kept every promise she made. I did, too. That was years and years ago. I wish I could find her.

With that said I have learned to avoid strippers. They live and die by the up-sell. That doesn't lend itself to the escort, amateur or SD / SB situation.

**Varoom** · 05-29-11 18:56

Originally Posted by fscott [View Original Post]

Now, to you, Literal. In my experience, every chat room, forum or other internet-based discussion group a "barn boss" emerges. My excuses to the rest of you earnest sd's, but that clearly is you. I am sorry to have intruded on you turf. I enjoy reading of your exploits, and will continue to do so, but will henceforth refrain from stealing focus. (edit delete)

Fscott doesn't seem to like the exchange in this thread. While Lit2 may have been suspect of ole fscott and his motives here, accurate or not, what fscott doesn't realize is Lit2 IS the Barn Boss here. He is the Barn Boss here because he started the thread on 12/26/10; it is HIS thread. The reason he started the thread is because the discourse of sb / sd didn't fit into the typical categories and others said, Go start your own thread. And he did. Kind of like coming into someone's house and telling them you don't like how they have the furniture arranged really. Not good form, as they say.

Seems as though fscott may be gone anyway, just dropped by and told Lit2 he doesn't like how he has his furniture arranged, and got up and left. Alrighty then. For the rest of us who have been around for any length of time, it seems that we like how you keep your furniture Lit2.

Originally Posted by Literal2 [View Original Post]

If so, I apologize.

Didn't mean / don't want to be barn boss.

No apology needed Lit2. It seems as though this little tif placed a bit of a damper on the info Lit2 was willing to share over the past week or so, almost in a concious effort to back off and not be the Barn Boss. But I think that most will agree with me, we appreciate and enjoy the way Lit2 has moderated, instructed, reported on your thrists, and overall conducted matters here in this thread. I for one feel that we are missing out on some reporting by Lit2 on his recent events with SB18. Oh and SB 11, or SB 4, etc, etc. In the words of Sgt Joe Friday (slightly altered);"Lets have the facts Lit2, just the facts." (and feel free to embellish the hell out of them for our reading pleasure). I for one appreciate Lit2 experience and efforts, both with the ladies and his willingness to share those experiences with the rest of us.

How do the rest of the contributors of this thread feel about this?

**CantWinLosin** · 05-29-11 14:31

My experience w / strippers is similar to Literal's, with the added caveat that they are usually more trouble than they're worth once you "catch" them. They are in that limbo between amateur and pro, with all the faults and few of the advantages of either one. Many of these girls have a deep-seated hatred of men, and that comes out in their dealings with us -- very mercenary, distrustful and lots of drama. I have a friend who spent much of her 20's as a dancer, and she admits that it took her well into her 40's to learn to ever trust a man or have a real relationship with one.

I make it a standing rule to not involve myself with dancers. There's too many other amateurs out there that don't come with all the baggage.

**Literal2** · 05-29-11 13:33

Originally Posted by Madaboutmax [View Original Post]

My experience, with the stripper type SB, has been that the retired, or soon to retire. 30 something girls tend to be the best. Old enough to not have unrealistic expectations on the value of their kitty, but young enough to still be hot and fun. I have 4 long term dancer / SB's that I have been with for over a year that range from 30 to early 40's.

I still enjoy chasing the hot 20 somethings, but they are flaky, full of drama, and lack skills in the bedroom. I guess I'm still chasing holy grail of SB's: " A hot 20 something body, with the sex drive of a 30 year old, the skills of a 40 year old and the grattitude of a 50 year old."

I found it took a long time and much moola spent in the VIP to develop relationships with strippers. As I posted earlier, I've had a total of four of these over the years. One was 22 with two kids and was looking for a nest but gave me the best BJ of my life. One was 19 and beautiful but wild beyond belief in her personal behavior and was self destructive. Both of these were short term affairs. Two older strippers, early thirties, lasted longer. One was engaged but after warning me not to get involved proceeded to get involved and cling. The other would not let me penetrate her with a condom on so there was a lot of HJ action. I will not bareback with any of these girls. One day she told me she could give me a child. I said no thanks. I saw her again a year later and she had her child, by another sc patron. Whew.

Earlier discussion on here about strippers concerned how hard is to fuck them. Some had my experience which was it takes a lot of warm up. Others seemed to be able to accelerate the process even avoiding buying any dances.

One great thing about dancers is you can check them out pretty thoroughly before you meet them alone and many have great bodies.

In recent years when I go to an sc, which isn't that often anymore, I try to spot the girls who will release you inside the club. This is less complicated for me, anyway. Others may have different experiences.