"Sugarbabies" / "Arrangements" Amateurs or Not?

I ran into similar a couple of years ago on SA. Was chatting with daughter, 19 or 20, didn't click so it didn't go further. A few weeks or so later start chatting with this 30 something young lady. She sends me her number to text, and it was already in my phone. I question her on it, says yeh, it's my daughter. I mentioned it was a bit odd, she commented a lot of guys like that. Sorry, I passed! After a few months, saw the daughter posting on BP, they were down on their luck and hitting bottom I guess. If they were both top shelf and good connection, I could see the draw to do a combo (not together though).

[QUOTE=ArcherSterling;2894014]This probably will sound like a letter to the Penthouse Forum based on that title!

I'll spare you the labor pains of how I got to this point, but I have found a 20-year-old SB and her 41-year-old mom -- who is actually hotter thanks to some bolt ons but to be fair has a prettier face -- both on seeking arrangement.

The daughter had agreed to meet me last night but then flaked agreed to meet me today, and told me I would only get to fuck her once, so I passed.

Mom is meeting me in about an hour, I made it clear in my messaging to her over the past few weeks what I was interested in, so I'm hoping after a couple of drinks and an appetizer I will be seeing the back of her head from various angles.

I am pretty sure they have no idea about the other being on there -- if they did, I would think the mom would want to know where her daughter was going last night -- if nothing else for safety reasons.

Plus, Daughter has been on the site for 18 months, mom less than two months, though she announced today she was deactivating her account and did.

How wild would it have been to bang a mom and daughter on the same day, six hours apart?[/QUOTE]

[QUOTE=JeezLizard;2895702]So just remember that as a mature SD you have a significant advantage when it comes to maturity and playing upon their psychology.[/QUOTE]Here is a text exchange with a 21 year old hard-body hottie at Boston Univ.

Well unfortunately I'm a hard woman to please.
Apr 28,2016.
4:48 PM.


Apr 28,2016.
4:51 PM.

That is a shame. How so? Maybe not. Maybe just a by product of dating clueless 20 somethings!
When was the last time you were properly fucked?



It's been a while. I've been fucked recently, just not necessarily sure if it's been done "properly".
Yesterday.
12:58 AM.



Yesterday.
1:19 AM.
Life is too short to have bad sex.


Couldn't agree wth you more. I wouldn't say it's been bad. Just not as satisfying as I would like it to be.
Yesterday.
3:24 PM.


Yesterday.
3:35 PM.
I love to pleasure and satisfy. Turns me on so much to know you are enjoying me as much as I am enjoying you. My satisfaction is guaranteed and easily achieved. But it is heightened experiencing yours.



I love how sophisticated you sound.
Yesterday.
11:55 PM.

And your confidence is such a turn on.




I rarely go for the college girls, but pretty much have the same conversation with any SB under 30.

Mom shows up, 40 minute later than the previously warned hour late.

Looks as pictured -- though when you arrive at a hotel bar at 940 pm with platinum curls, short skirt, skimpy top, big cans and lots of make up, you can leave the wrong impression! At least she pulled up in a Mercedes!

Shared a drink, chatted about stuff, but she made it clear no BCD on first meeting. Crapped out.

After I gave her a kiss goodbye she said "my "friend" told me she was supposed to meet you today -- how many hook ups have you had since you've been in town?" I told her the truth -- she blew me off -- but refrained from telling her she was willing to give me anal for a $300 one hour visit and that I knew she was her daughter.

Fortunately, I had a back up plan who was quite happy to bang me senseless after one drink. By far the hottest body and prettiest face I have encountered in the Bowl. Almost got her again on my way out of town the next morning.

And for those inquiring minds -- the mom is off SA, the daughter is still on, NC baby in W-S. But she only offers one round even if she meets you for 3 hours.

Good luck!

[QUOTE=JeezLizard;2891303]Is to cum in their mouth. When I can't do that, I pull out.

I lost count of how many total women I've had sex with sometime when I was in my 20's, I almost always bareback because I'm not a fan of the wrapper. The only time I got anyone pregnant I was a drunken idiot and got in the habit of cumming inside (not at her request, just my own laziness) even when I knew her depo provera shot was no longer protecting her. Thankfully she aborted and I learned my lesson.

It's either going in their mouth, or on their ass / face / tits / tummy whatever.

The effectiveness of the withdrawal method is underrated.[/QUOTE]I am also not a fan of the wrapper but I solved the birth control issue when I first started into the bowl a year ago with a vasectomy. Easily done and painless though I realize many brothers may not be at the right time of life for this personal decision. I have one drunken idiot story to share. I was 19 in my fraternity house bedroom with an 18 yr old first date. We were both wasted (drunk and stoned). I used a condom but then fell asleep for the night with her in my arms. The next morning I woke up but could not find the (used) condom. Figured it was in the sheets someplace but after she headed bck to her dorm I still could not find it. The next night we get together again in my room and I do a careful FIV. Yes you guessed it. The condom was still inside her! I carefully take it out but as a chicken shit 19 year old I don't tell her. Sure enough, 6 weeks later she tells me she is pregnant. Fortunately (roe vs wade had just passed and abortions were legal in ny so she went with a gf and had it done. We continued into a 3 year college relationship even when she had to transfer the very next semester to another college 2 hours away in order to live at home.

I actually banged a mom and daughter a few years ago from tagged. Hopped on, met e daughter was fucking within the hour. Left her, still hungry. Hopped back on tag and found a hot older woman. While flirting and browsing her profile I noticed a pic of her daughter I had recently fucked. Got her number anyway. Ended up going to the exact same apartment the daughter was at. It was about midnight at this point. Went straight to mom's room and ***** her out. Snuck out hastily before morning as to not alert the daughter. I still don't think they know about each other. Got the mom again about 5 months ago.

[QUOTE=ArcherSterling;2894014]This probably will sound like a letter to the Penthouse Forum based on that title!

I'll spare you the labor pains of how I got to this point, but I have found a 20-year-old SB and her 41-year-old mom -- who is actually hotter thanks to some bolt ons but to be fair has a prettier face -- both on seeking arrangement.

The daughter had agreed to meet me last night but then flaked agreed to meet me today, and told me I would only get to fuck her once, so I passed.

Mom is meeting me in about an hour, I made it clear in my messaging to her over the past few weeks what I was interested in, so I'm hoping after a couple of drinks and an appetizer I will be seeing the back of her head from various angles.

I am pretty sure they have no idea about the other being on there -- if they did, I would think the mom would want to know where her daughter was going last night -- if nothing else for safety reasons.

Plus, Daughter has been on the site for 18 months, mom less than two months, though she announced today she was deactivating her account and did.

How wild would it have been to bang a mom and daughter on the same day, six hours apart?[/QUOTE]

Funny, situation I was in, I didn't want any part of the mother daughter thing, just didn't feel right. Your situation, same place, the excitement. Oh yeah, that sounded like fun! What a memory!

[QUOTE=PassinHoes;2896521]I actually banged a mom and daughter a few years ago from tagged. Hopped on, met e daughter was fucking within the hour. Left her, still hungry. Hopped back on tag and found a hot older woman. While flirting and browsing her profile I noticed a pic of her daughter I had recently fucked. Got her number anyway. Ended up going to the exact same apartment the daughter was at. It was about midnight at this point. Went straight to mom's room and ***** her out. Snuck out hastily before morning as to not alert the daughter. I still don't think they know about each other. Got the mom again about 5 months ago.[/QUOTE]

A first for me having a 22 yo VCU SB end up as a UTR. We are at our M&G dinner at a steakhouse. Things are going great with both of us laughing and would not have a clue that we just met. While waiting for the check, she starts rubbing my leg with her foot and saying she wasn't in a hurry to get back to studying for exams. I winked at her and said there a hotel across the street. She said let's go!

No mention of money beforehand so I am thinking I'm finally going to get some sugar for just the cost of dinner. So we get in the elevator and she's already kissing me. Once in the room it's clothes flying off and we end up on the bed all wrapped in each others arms and kissing like crazy. After a few minutes we end up with her on top of me rubbing her shaved kitty on my shaft. She leans in close and whispers in my ear that it is $ for a BJ and $$ for a fuck. Of course by now my little head is in full control and I say fuck. She rolls off me and grabs her purse. Out comes the condom and some lube. Then she proceeded to ride me. I think she was thinking that being an old guy and she being so young that I would pop quick. But I made her work for it and she was getting real tired when I finally shot my load.

Anyway, it was a nice evening and she sure knew how to play me. We will meet up again next week when I plan to sample her full menu. Willing to share her info with other senior members who have college cuties to trade info on in the Richmond / Charlottesville area.

[QUOTE=ToeLover57;2899625]No mention of money beforehand so I am thinking I'm finally going to get some sugar for just the cost of dinner. [/QUOTE]Ah hem.

[QUOTE=ToeLover57;2899625]Anyway, it was a nice evening and she sure knew how to play me. We will meet up again next week when I plan to sample her full menu. [/QUOTE]I am just curious why you would see her again if she knows how to play you? Is there a risk she plays the same game and in mid stroke ups the ante? Aren't you afraid you are setting yourself up to be rinsed by her and others?

[QUOTE=CephlapodLove;2899865]Ah hem.

I am just curious why you would see her again if she knows how to play you? Is there a risk she plays the same game and in mid stroke ups the ante? Aren't you afraid you are setting yourself up to be rinsed by her and others?[/QUOTE]I still liked her better than what I have been seeing on BP for more money. And she is a better dinner date than most SB's I have seen.

[QUOTE=ToeLover57;2899625]A first for me having a 22 yo VCU SB end up as a UTR. We are at our M&G dinner at a steakhouse. Things are going great with both of us laughing and would not have a clue that we just met. While waiting for the check, she starts rubbing my leg with her foot and saying she wasn't in a hurry to get back to studying for exams. I winked at her and said there a hotel across the street. She said let's go!

No mention of money beforehand so I am thinking I'm finally going to get some sugar for just the cost of dinner. So we get in the elevator and she's already kissing me. Once in the room it's clothes flying off and we end up on the bed all wrapped in each others arms and kissing like crazy. After a few minutes we end up with her on top of me rubbing her shaved kitty on my shaft. She leans in close and whispers in my ear that it is $ for a BJ and $$ for a fuck. Of course by now my little head is in full control and I say fuck. She rolls off me and grabs her purse. Out comes the condom and some lube. Then she proceeded to ride me. I think she was thinking that being an old guy and she being so young that I would pop quick. But I made her work for it and she was getting real tired when I finally shot my load.

Anyway, it was a nice evening and she sure knew how to play me. We will meet up again next week when I plan to sample her full menu. Willing to share her info with other senior members who have college cuties to trade info on in the Richmond / Charlottesville area.[/QUOTE]I'll update this report by saying I was surprised how well she came across as the innocent college student in our messages beforehand. Most don't spend much time messaging first.

[QUOTE=ToeLover57;2900975]I'll update this report by saying I was surprised how well she came across as the innocent college student in our messages beforehand. Most don't spend much time messaging first.[/QUOTE]Most are utr. If they have more than one daddy they are utr. A lot get straight to the point because they have been screwed over but the smart ones play the innocent card. Great selling tool and usually brings higher bucks.

[QUOTE=PassinHoes;2896521]I actually banged a mom and daughter a few years ago from tagged.[/QUOTE]

[QUOTE=ArcherSterling;2894014] I have found a 20-year-old SB and her 41-year-old mom -- who is actually hotter thanks to some bolt ons but to be fair has a prettier face -- both on seeking arrangement.How wild would it have been to bang a mom and daughter on the same day, six hours apart?[/QUOTE]You both are living my dream life.

[QUOTE=ArcherSterling;2894026]For hotels, a couple of options have worked for me.I own my own business, so I will book a hotel room on Hotel.com if the wife ever came to the office and saw my business credit card statements I would just say it's for one of my employees elsewhere in the US since [URL]hotels.com[/URL] doesn't show the specific location on the transaction.

I don't worry so much about showing my I'd. The bigger risk, if any, is in running into someone I know in the hotel lobby might be there for a meeting or conference are visiting a friend who's in from out-of-town. I will than a much much much smaller market than Charlotte so this is a real possibility so I have to be sure to pick discreetly located hotels were no one will see my car in the parking lot. The hotel across from Sam's Club is perfect for this so I can park in the Sam's lot and walk over.

Depending on your SB, and the younger they are the less they seem to care about their anonymity, is you book the hotel and their name. The only catch here, is even if you prepay the room on [URL]hotels.com[/URL], they usually ask for a credit card or debit card at check in to cover any quote incidental charges" this is less of a problem in the mid to lower scale properties that don't have room service or other things that end up on your room account, and they are set up to deal with the lower end of the economic scale and just block long distance calls pay-per-view and other billable items in your room.

My favorite is to play on pm am Double-header. Book the room after lunch, fuck for a few hours, and she can either go home and meet you again the next morning for another Fuck fest or you can line up a warning event with the second girl. Meet at nine you can usually get a check out at noon, bada bing, bad a boom, two rounds of fun for the price of one-at least on the hotel side. I have had some stay over and see them the next morning, but I make the two rounds and all-inclusive price for her tuition assistance grant. If I really like them or think they are worth the expenditure, I'll put them in a nicer hotel in a more happening part of town, and give them 50 bucks to go out and have dinner since I can't be with them.

Hope that helps.[/QUOTE]Those are good advice to take, if your booking hotels to do the deed with any SP.

Haven't had a FC with my LTR SB in some time. We linked up recently after she came over from a night clubbing. She was more explicit than ever before and porn star quality. It was the best sex I ever had and she was doing just about everything. I had no idea she had this type of performance in her. She was vocal and saying stuff like "this pussy is yours, no one else's", etc. You get the picture. The session left me mind-boggled. Was she holding back all the times before? Was it because she felt I was drifting away? I'm not sure, but she's been distant after the session and it left me wanted MORE.

I have no idea if she's back playing the field and learnt some new thing from one of the Bros. Or what. Anyways, she's leaving for a few months for a summer school program. She made no requests for sugar and I don't know if she's ready to move back in as the SB / SO / GFE role. I've been trying to replace her, but SA hasn't been too fruitful as far as inventory. I'm stuck at this point.

She left most of her clothes and belongings at my place, same as before we had a falling out. The main reason for our break-up was she spent far too much time with her peer group. While we were living together she had a habit of disappearing. She'd claim she would be staying at a girlfriends. We haven't seen much of each other because she claimed she needed space and living together with my "rules" was too much for her. She hasn't had access to my sugar and I don't know how she's dealing with bills.

I'm always hands-off with my SBs. I don't call or text them too often. I do this to not seem needy. I think I fell for her, especially after a round of renewing my SA and not finding the same 10/10/10 quality out there. This girl gave me the emotional, sexual connection I needed. The complete package and everything I wanted out a SB. I'm wondering if she found a better SB or if she's changed her mind about our SB / SD as an exclusive SO arrangement. I'm only hopeful that she'll come back around for the fall semester.

Any suggestions to fix this drought I'm in?

[QUOTE=JeezLizard;2895702]I'm guilty of this too: looking at some of these young, firm students and wondering if my cock even deserves such tight, un-indoctrined to the rest of the world, pussy.

Don't underestimate the value of your own maturity as an aphrodisiac to them. Every now and then I put these SBs to the test as to why they should have a genuine interest in me beyond financial aspects, because they are young and hot and have so many pursuers.

Sometimes they send me actual screenshots of the shit these 18-22 year old dudes send them on their phones, or maybe they cut and paste their email (be careful of that if you ever use your real name by the way). And while I'm sure I'm sure they get some "good" messages they don't care to share, most of the time they are using this as evidence as to why they want to date someone up to their standard. Believe me if you saw the ridiculous attempts at getting pussy the average under 35 year old guy writes (and believe me I see a lot, they send me the transcripts) you would probably feel a lot better about your own intellect. Then there is facebook. What an incredible tool for the average SD. Some of these girls have these boyfriends or ex boyfriends that look like I could pick them up with one hand and shake them like a baby, but not the kind of baby I want. Some of these little twerps have more tattoo ink on their fucking bodies than dudes born in the 60's or prior have horny blood in their veins. No competition.

So just remember that as a mature SD you have a significant advantage when it comes to maturity and playing upon their psychology.[/QUOTE]Its easy to forget the plus you have as an SD. These girls are scrambling to pay cellphone bills and pocket money for a decent lifestyle. I did some PI work on my LTR and discovered info on her ex-boyfriend. He's a decent chap and excelled academically. He can't offer her the type of lifestyle I made her accustomed to. I didn't do anything phenomenal, but I offered her housing in a luxury condo, access to luxury cars she wouldn't drive otherwise. With me she also knew that I'd cover a shopping trip on the mall and money for her regular upkeep. It wasn't a lot out of pocket compared to a pay-per-date situation. Her dating other guys in her social circle may give her more social relatablility to her age group. Because of the age difference we're out of touch about music and social media accounts like Instagram and Facebook posts. The benefit I brought was safety and security. With me she wasn't worried about her cellphone being cut off. She knew she was good for food, dining out and pocket cash. I can't say the sex is better. My erections at late 30's aren't like when I was in my 20's and could go round after round. I take it as a plus that she could have sex in a proper bed, a guy with no roommates or competing 20 something girlfriends.

There was no drama in the relationship. Perhaps a routine with a SD can get dull. I can't gauge if her normal boyfriend types were better or not. I can only judge by her actions. She'd occasionally go dark. I don't know if she was seeing other guys. I have no proof. I only caught her being distant and chatty on her phone. It didn't bother me enough to want to see her text messages or try to crack her email accounts. 20 somethings operate in mystery. I can say that it added some excite be about the unknown. I can only attest to the younger SBs being more fun than women my age. I don't believe I can ever go back to dating my age. These girls bring firm bodies, great sex to the table. The psychological game of if she's trying to fleece me for my cash sucks. Overall, the experience seems worth the gamble.

I probably should be more confident in what I bring to the table. Women in general go off emotion. They use no logic or reasoning in how they go about things. One would think they'd be more submissive to an SD. These girls are wild and can't be tamed. There's nothing you can really do about. It's better to just be in the moment and enjoy the joy and fun they bring. It took some learning, but I no longer question there whereabouts and if they are really being exclusive. Doing that comes off as insecure and the last thing you want is to come off as needy. Once seen as needy or dependent on them, it's all downhill. Several lessons learned from my time in The Bowl.

A follow-up to my adventure with Mary. After a week, she overcame her moral qualms and we got lost in the Funhouse for another month until just a few days ago when she asked for extra money and I said I could not and she abruptly ended the relationship. Despite having often expressed admiration for me and enthusiasm for our meetings she suddenly became cold and told me to leave her alone. It was not the first time she had asked for extra money. She was very needy and demanding. All in all, I was spending over $1200 per month on her, which I can sustain for a few months but not indefinitely on my income. One advice I can offer to the forum is to have a budget and stick to it, even if that means you cannot afford a sugar baby. Now that looks like the case for me, at least not an exclusive hot 19 year old SB. Maybe a non-exclusive late-20's single mom would be more appreciative of my limited offer.

Also, it's important to guard your emotions. I don't feel too bad now because she was very cold in the end, and due to the fact that I'm relieved to get back to saving money for awhile. By August I should be back, financially, to where I was in January. Mary had several personal problems, some severe, which I won't go into here. But I think that quite a few SBs have problematic backgrounds and its something to keep in mind and be sympathetic to.

[QUOTE=Snake27;2846920]I've been out of the "monger" game for a few years now, but I've often been tempted by the rise of the sugarbaby (SB) online world. I had a few (3) SB relationships via the bar scene years ago, and almost feel like I "invented" the concept. Based on the reports here, it seems so much easier and efficient online.

I made a profile on SD4 M, it seemed to be less overhead than SA, though I've heard that SA is more of a college crowd which would be better for me. I may try SA later. My profile pic was a software blend of my face and another guy's face. I texted or emailed about 20 girls in the area, met three from the site, and had one SB relationship lasting two months, which ended strangely. Let's call her Mary. She was 19 and told me I was her third sexual partner.

It was nice while it lasted. A true GFE: kissing, friendship, wet pussy, orgasms, etc. She was intelligent, which I liked. Mary's SD4 M profile went unused during the time I knew her. The other SB prospects I met seemed to be professional SB, as they remained active online during the time I was on the site. Mary said she wanted to be monogamous with her SD. At my age (early 50's) it was amazing to find an attractive 19 yo who responded to me like that. I'm pretty sure it was real.

After two months, Mary called it off, citing moral qualms about taking money from my family. She was also unhappy with how much I paid her (200/ visit / week). But after breaking up, a remarkable sequence of events occurred. I was contacted by a friend in her dormitory, also a cute college freshman, who said my offer was adequate and she thought I was handsome. I was tempted, but it just seemed too weird for me, so I passed. Within a few days this led to more strange events: Mary trying to get back with me, her dorm friend sending angry messages (thank goodness for anonymous phone / email) and finally Mary giving up again.

I'd like to have one SB who is at least semi-normal and remain with her for a long time, but without getting too serious and as long as she accepts my budget. I think I'll try again.[/QUOTE]