"Sugarbabies" / "Arrangements" Amateurs or Not?

[HollywoodGuy]

Not a lot to report. It seems all the hot girls are turning down my offer lately (and there are so many really hot new girls on the site) and about half of them are UTR's but I wouldn't mind a one night stand with a hottie. But not paying $$ again. Seems to be the going rate these days. The last one was beautiful but it didn't rock my boat.

In spite of that I got a reply from a POT on Sat. And saw her on Sunday and Monday. She turned out to be a 24 year old mixed AA / Cuban 6.5/6.5/7/?. We kissed a little and talked a lot. I just wasn't feelin it. So I am done with her. No sugar, so except for one beer the first night, no money spent at all. The only interesting thing about this was we met without ever talking on the phone. Just txting.

Got what looks to be a 22 year old mixed AA / Guatemalan maybe 8/8/8/? HYM. I think she is UTR because she is driving 80 miles RT to see me for $. This is basically a straight to the FC type of date. But you never know. She seems pretty real and knows the score.

Work pressures really just make me want to stick to my regulars. But I feel like if I don't get out there once a week or so I am losing my edge. But I do like the familiarity of my regular girls. No drama, good sex, and no drama. LOL.

[BigTigger]

MsBubbly. Flaking out on me. Can't seem to nail her down for a date. She is communicating, but I think has either cold feet or a better offer.

MsSlimCheerleader. Asked for money for Christmas shopping for kid. I was a little suspect, then she said $45. I eventually gave it over and today she showed me some of the gifts and was very happy that I helped her finish all her shopping. Wow...$45. She is way ahead on this one.

MsVanity. Will not be happy, I cannot meet her Thursday morning, but I have not told her yet. I'm waffling, because I'm supposed to see MsSlimCheerleader and she's assertively trying to make that happen.

MsHipsnThighs. Checked in with me today. Just being nice of course after we decided to part ways. I can definitely see her being open any time I want to stop by and get a great lay!

MsCelibate. Time with her was good. But not quite as magical as the first time. She has some weird ways about her, and her mouth can be a little untamed when she decides she want to pick at a person. Her oral skills were good and her sounds are great. So I'll keep it around for once a week thing. She even offered to pay for the hotel and go 1/2 on food. I did not let her do it, but it was a great offer.

BigTigg.

[BigTigger]

Lots of texts and pics today. I asked them both to give me a list of gifts I can choose from when I want to surprise them. They seemed to really enjoy this exercise, even comparing notes and the like. They both are really excited about meeting. The flirting from both have intensified and of course I've played along. The pics they have sent have allowed me to see more of their bodies, but always with clothes on and nothing to risque, LOL. So I can see the DDs from MsChocolate because she sent it in tight workout clothes. MsCaramel did show a little cleavage, but even that was tame.

Seems to be some sort of sex discussion daily with lots of areas that seem very compatible. Both said they make lots of noises. If it's good... So we'll see. They were very clear, they do not do each other, so this will be interesting to see how this works out.

So we are schedule to meet next week as my schedule is crazy. But I do like the way things seem to be headed.

BT.

[HollywoodGuy]

Has anyone tried this site called Milfaholic? They seem to have a lot of very nice looking MILFs and they are local.

Not sure the sucess rate but there does seem to be a lot of horny MILFs on there. They start out with a lot of rated R or even X pics.

Curious about whether it is any good.

Revvo.

Those sites are scammy.

[BigTigger]

As I'm not 100% sure about this kind of thing, I think it needs its own posts separate from my others as this could end up being a full blown 3 some relationship. Sounds TGTBT. So I'll just update this individually.

So let's start by giving them names. Hm. One is light brown and the other is more dark brown. So we'll just go with MsCaramel and MsChocolate.

So exchanged texts with both today. MsCaramel was supposed to send some additional pics. She had some pressing issues with school and she eventually sent them today. The one thing I've noticed about both is that they seem very genuine. None of the photos come across as super flirty or true SB type of pics. They are all normal 20 year old girls, with conservative looks. Not much skin and not suggestive at all. Just pics they take on campus in daily life smiling.

I actually talked to MsChocolate on the phone for about 15 minutes. During that time, MsCaramel sent me a IM from the library. They claimed not to know the other was communicating, I said "yeah right", then I did get a good laugh because they both said the same thing. If they had planned it, I'm guessing they would have planned to use a different line, LOL.

They both are ready to get the first meeting out the way and have complimented me on how comfortable I made them. I do have the fortune of following a jerk. The first guy they met like this, talked a 1/2 good game, played his cards close to the vest, did not ask a bunch of questions and didn't seem as interested in their lives as me. The first meeting, they get to the room and without any warning, just asks them to get naked, LOL. In the end, they did not get undressed, told him that that is not what they had in mind and decided to leave. He did pay for their travel, but it was awkward and uncomfortable for them both. Mainly because they did not talk about it in advance and he made them feel like prostitutes in stead of SD / SB relationship. (I know..I know..we have had this discussion thousands of times, SB=Prostitute...LOL).

At this point my flirting, joking and seriously being interested in their lives will have them taking their clothes off on the first date without prompting from me. They do both seem eager. I still have my spidey radar up, so we'll see how it goes. They are 2 1/2 hours away from me. So it's taking some coordinating to meet up as I have a busy week this week. They are 2 1/2 hours away in the opposite direction of the TiggaPad. So 4 hours from there, so that's a no go. But they are willing to drive and use public transportation. So once I can get this first meeting out the way, we are on!

BigTigg.

[BigTigger]

So MsBubbly canceled out on me that morning. I had already cut off the second session with MsCelibate in hopes of landing MsBubbly. However, I did not go back and hit MsCelibate again as she has the 38 year old MILF body of the group and my interest sexually was waning some. She's pretty, but after a few hard bodies that I've been around, it's hard for her to compare.

This week is crazy busy for me at work, so not sure how things will shake out. Supposed to have MsVanity, MsBody and MsSlimCheerleader this week. There is not way I'm doing all of them, if any of them really. More than likely it will be MsSlimCheerleader on Thursday night.

I had my breakup email exchange with MsTripleDs. Basically she got uptight with something I said via email. Instead of chatting, she ignored me...for (2 weeks! Then after 2 weeks after she has recovered she wants to chat. She never addressed my original issues and is a self-proclaimed passive-aggressive conflict manager, LOL. I told her that I can't deal with women like that and that her actions just turned me off. She missed 3 dates and in general was annoying. She wished me the best and I did the same.

BT.

[Dog Rice]

Did a quick look on google, and does not seem to have good feedback: http://www.scambook.com/company/repo.../Milfaholiccom.

Has anyone tried this site called Milfaholic? They seem to have a lot of very nice looking MILFs and they are local.

Not sure the sucess rate but there does seem to be a lot of horny MILFs on there. They start out with a lot of rated R or even X pics.

Curious about whether it is any good.

Revvo.

[Revvo]

Has anyone tried this site called Milfaholic? They seem to have a lot of very nice looking MILFs and they are local.

Not sure the sucess rate but there does seem to be a lot of horny MILFs on there. They start out with a lot of rated R or even X pics.

Curious about whether it is any good.

Revvo.

[BikeRider]

So I checked out the profile of two 20 year olds presenting themselves as a package. I did not send a message. They eventually sent me one. We talked on the phone and I am still stunned at the opportunity.

2 20 year olds college cuties, willing to drive, looking for experiences, not a couple and are fine splitting $100-$150 per visit. We talked through a lot of sex questions, to make sure we are compatible.

It will cost more for meals, etc. But I am willing to try. They are willing to visit my area twice a month.

I will keep you updated.

BT.

BT. They've been on my radar as well. I've just been too busy to follow through so far.

[BigTigger]

MsCelibate Sun 4 pm. Tiggabounce.

MsBubbly Sun 8 pm. Tiggabounce.

MsBody Mon 8 pm. Date only.

MsVanity Thurs Morn. Tiggabounce.

TheDuo. TBD.

MsSlimCheerleader. TBD.

[J Martinez]

... 2 20 year olds college cuties, willing to drive, looking for experiences, not a couple and are fine splitting $100-$150 per visit. We talked through a lot of sex questions, to make sure we are compatible.

It will cost more for meals, etc. But I am willing to try. They are willing to visit my area twice a month.

I will keep you updated.

BT.

If this works out the way most of us are thinking. You're one darn lucky dude!!

[BigTigger]

So I checked out the profile of two 20 year olds presenting themselves as a package. I did not send a message. They eventually sent me one. We talked on the phone and I am still stunned at the opportunity.

2 20 year olds college cuties, willing to drive, looking for experiences, not a couple and are fine splitting $100-$150 per visit. We talked through a lot of sex questions, to make sure we are compatible.

It will cost more for meals, etc. But I am willing to try. They are willing to visit my area twice a month.

I will keep you updated.

BT.

[BigTigger]

Keep up the good fight. It's her loss. How is the new apartment going? I checked on craigslist here and I have seen some nice rooms in a house for around 400 to 500 with no lease. I am thinking about it myself.

Revvo

Ok she turned out to be a real keeper. I told her it felt one-sided and she agreed and says she doesn't even count that as being intimate. Is ready to redeem herself. With an interesting twist we had a date scheduled for my move in day to my place. But she was on her period. So I made it clear that I expected oral before the night was over and she had to initiate. So I was late because of work, got my key to the place and picked her up. We had dinner at a Hibachi (which I'm finding is a great date spot) and wet shopping for my new room at Wal-mart. Picked her up a few things. We got back to the room, put some things together...mainly the bed sheets and comforter. The she proceeds to work me over orally...and swallowed every drop. Wow! She definitely made up for her lackluster first time. She even got a code name MsSllimCheerleader. Gave her $ and she was thrilled. We talk / text everyday and are working on linking up on a regular basis.

By the way, the room is working out great. My roommate did not even look over from the couch when we walked in or out. I closed the door to the hallway that lead to the room and had a ball. Cash only, safe and discreet.

Had a M&G with one I'll call MsBubbly. She is 26 year old AA, she has a head full of bouncy curls, big beautiful smile and just a bubbly personality. We had breakfast, laughed got along really well. I found a nice spot for us to talk and before it was completely over we had two very long kisses. She's extremely sexual and is ready to get to it immediately. She says it's been a while since she's been licked good.

In the end, I'm probably going to end up with a rotation of 4 in no particular order. All for $ or less per visit. I'd like to cut this down to 2. Oh MsBody contacted me, she wants to try again. Not sure if you remember. Face is ok, but the body is a 10! Knowing me, I'll find a way to meet her when I should be focused on the rotation.

MsSlimCheerleader.

MsVanity.

MsBubbly.

MsCelibate.

BigTigg.

[BigTigger]

Too much to update all in one sitting, so I'll use a combination of twitter like update and full explanations.

MsThickness. Had text exchange with her that highlighted her flakiness. She's a great lay, but just too undependable. I pretty much just stopped returning her texts. She left me hanging and disappeared and didn't really have great explanations. I trying to narrow this down to someone consistent and dependable. She's not quite there yet.

MsHipsnThighs. I got tired of having sneak past her room mates, sneak to the shower and then she messed up a date we had scheduled. I planned the time, had a full two hours scheduled at her place. She lost track of time, didn't update me until the last minute and eventually wasn't available until an hour later. She was like "I was only an hour late. And I was like, "yeah, but it's only a 2 hour date!" Tried to move her to booty call only and she declined.

MsLilMama- The girlfriend has taken all of her free time and she has to sneak around like she's married. She had major money problems, but could not assure me that if I gave her more or fixed her problems that I could see her more. So I cut off all funds unless we see each other. I spent over 1 k on her the first month, thinking she was long term, to only find out that the girlfriend hinders her actions and availability. Plus she's taking to being bratty and spoiled (her words) in the bedroom. So the sex is very blah-blah now. There really isn't a reason to see her anymore.

MsTripleDs. Exchanged STD test and she told me of the IUD. Met for the first real date that included overnight. Hit it 3 different times throughout the night and morning. She then gets flaky on me saying that she sees me different now because I trusted her and came inside of her. Was I supposed to ask for medical information to prove the IUD? She then missed a few dates, declined a few dates, then got mad when I called her out. I've moved on.

MsCelibate. Another interesting story. Older MILF (38 years old). I'd give the body a 7.5. For a number of moral and religious reasons had been celibate for over 10 years. After first lunch date and some phone chatting / flirting she decided I was the one to wake up the kitty. She has her own place and is a not drama type. The sexy was good. I took it easy on her, she really responded to the oral and we had a ball. We are scheduled to link up again this Sunday. She's been very clear. She will screw my brains out as often as possible, but will not get attached. So it's kinda NSA. No funds have been exchanged. I just cover all expenses.

MsVanity--African descent. Shows up with blond hair, nails done, color contacts, etc. She's short with a big butt. We met for a M&G at Chipotle of all places. Laughed and joked. Chemistry was there, but the goodbye kiss was a bit rough. Since that time, almost 2 weeks now, we've been in contact. We are scheduled to meet Thursday morning. She wants to see my new place and get a good sticking. She admitted today after sending a few nasty pics, that she really likes sex. This came out after I offered to meet for dinner tonight while she's on her period. She declined and would rather wait until she cold get the Tiggabounce.

MsGermanChocolate-This one was weird (German Background, likes black men). Caucasian, 5'7, nice body, thick legs and little belly fat. Treated her dog like a child. Brought the dog on the first date. We ate outside for the date, so it was cool. Conversation was good, but she was dealing with somethings. Let me know that she was leaving for NYC in 2 weeks and would be back 2 days a week. She ordered a big expensive meal, 3 glasses of wine. At the end, she was a bit put off that I gave her a kiss goodbye and that I would not kiss the dog (REALLY! She invites me back the next day to come to her place. So I pick up condoms, take off work and meet her at the liquor store on the ground floor of her building. I buy a $45 bottle of some small hard liquor (I don't drink). I also brought lunch. We get up to her place and she's eating on the couch while I'm watching TV. She then makes a comment, "it's too bad that you don't get off on watching women eat, I'd love that". I was like no, I get off on actual "sex". She eventually tells me that she's on her period (they all say that). I say cool, well we can kiss some. Kissing was horrible, then she interrupts me to say that she needs help with rent money. She needs $475. I explained to her that we had just met the day before and we have yet to even be intimate. She agrees and acknowledges the awkwardness of it. Then suddenly she has to get back to work. We were supposed to be together for 4 hours, turned into hour and 5 minutes. I spent more time in traffic in DC. She then does not return my calls or emails. I sent one this morning as I was deleting entries and she say "Jesus, I'm not interested!" , I just replied with "OK" and deleted her information.

[Pats Fan1]

I have a medical condition which flares up once every couple of years (no it is not STD or penis related). It is painful and prevents me from having sex for about a week. I have a SB 2. I have written about her and posted a few pics in the last couple of weeks. I talk to her about every day. She is a totally hot young baby. But she is also a cool chick with a good sense of humor and always a positive attitude. Rare is today's world.

So we get along great. She lives about 2 hrs from me and I see her 1 x per week. So she is fully aware that I'm having a medical issue right now and next week I'm in FL. So she's getting no sugar for 2 weeks. I'm in her area on Thurs and have suggested I take her to lunch which she is excited about. Then it struck me maybe she's thinking I'll give her full sugar for just having lunch? I hope not. I made it clear up front that from my end I was looking for adult fun as her consideration. Obviously, I'm buying lunch and I'm excited about being at lunch with a hot babe half my age. I was thinking of getting a funny card and putting a gift card of a token amount in there. I usually give her 150 sugar. I was thinking more like 50 gift card to a tanning place she visits. What do you guys think?

So I met with SB2 for lunch. Thanks for the feedback from you guys. I opted to go forward and not talk to her about it first. I just brought the card and a $50 gift card inside. It was hard to tell beforehand how it was going to go over. She's a spoiled girl. About a week ago Daddy paid $10 k for her get veneers. They look great by the way. So we have lunch and I give her the card she loved it. She wasn't expecting anything at all which is cool. After lunch she spent 10 minutes in the car with me making out. She played with the stick shift a little bit but I had to get my business appt. She said she was really horny and couldn't wait until I got back form FL. I think she is just using me for the sex and who am I to complain?