This is part 2 of the Sugar Bro series. Mike has given up on the hit and miss of the dating scene. Sometimes going weeks without sex. He has decided to go the Sugar Daddy route and fund some hot young things education in exchange for regular pussy.
Sugar Bro 2 (The Interviews)
On the plane home I started to do some research on how to be a Sugar Daddy. There are two universities near where I live so I thought I would look to see if they had a local newspaper that would take classified ads. Each school had two or three local newspaper, that I was able to access on-line. I pulled up one of the papers, and went to their classified pages, and found no less then 3 ads from 2 girls, and 1 guy looking for a sugar daddy. Both of the female ads listed a private posting board where I was to leave a message. No way around it at some point I would have to list a contact phone number. Maybe I was over thinking it, but I didn’t want to list my cell number, so I will have to pick up a burner phone once on the ground. I went through the other school papers and found 7 girls looking for a Sugar Daddy. They all had similar contact requirements, so I posted to all seven of them and waited. On the third day I got a picture of a girl on my burner. She was wearing a bikini, looked very asian, young with long dark hair and a great body. Her message was Hi Daddy, can you afford me? I responded with a pic of me at the beach in trunks and bear chest. Then I said yes I’m sure I can afford you, but are you worth it. What are your needs? She came back with tuition, books, rent, and 3g’s a month allowance. She then asked me is my picture current, you look really young for a Sugar Daddy? Yep I answered I’m 28, work in high tech. You can call me Sugar Bro. Where can we meet, she asked. I responded with I’m interviewing a few others girls. Booked up for a few days. How about a drink at Cork & Crown a local Pub near her school later today say 5:00 PM. Sorry for the short notice, but like I said busy for a few days. Ok she said I know the place. See you there.
I was sitting at a booth in the back of the tavern working on my laptop, keeping an eye on the door. For some reason the place was not busy, with only a few people hanging around the bar. The door opened and two asian girls came in. I recognized her right away from the picture she posted. Maybe 5’5” or 6 with large tits for her build. Very slim waste. Beautiful eyes that were very alert. Taking in everything as she looked around, obviously looking for me. Between the two of them the other girl was stunning, with a body that was almost hourglass. She pealed off and went over to the bar, as my girl saw me and headed my way. I stood up and introduced myself as Mike, shaking her hand. Hi she said nice to meet you my name is Sunji. I was drinking coffee and she said that was fine, so I flagged the waitress for a second cup. She got right to the point, your not what I had in mind for what a Sugar Daddy would be. Old rich guy looking to date a pretty young thing. Well I’m a young rich guy who doesn’t have time or the interest in a long term relationship at this time of my life. Dating is such a chore, and it’s so hit and miss. I am more then willing to pay, for a pretty young thing on retainer so to speak. If this goes forward you would have to be available upon my reasonable request. I will tell you now that could be several times a week. So she says what will you be looking for on these dates. Companionship, oral, anal, and vaginal sex. Oh she said I don’t do anal. You don’t know what your missing I said. Ok she said we can talk about that. You will need to see my doctor every month, to be checked for STD’s, and he will give you a monthly birth control shot. Your job will be to look and dress your best when we go out, and to satisfy my needs. I will give you a credit card to refresh your wardrobe, with a couple of cocktail dresses, underwear, negligees. Do you live alone I asked. She nodded yes and then looked over at the other girl giving her the high sign that she could leave.
Look I said I’ve never been a Sugar Daddy before, but we are talking about tens of thousands of dollars investment in your ability to satisfy my needs. I want you to look like eye candy on my arm when we go out. You are a beautiful young lady, but can you make me look good, and make me feel good, and sexually satisfy me when I need you. I’m a good guy, you will never have to fear me, as I will treat you like a princess. I will need you to sign a legal contract. It is a contract developed by the Sugar Daddy App people. I like the way your hair looks and would like you to keep it that way. How many years of school do you have left? Are you screwing anybody now? If you are that has to stop. Your physical commitment has to belong to me, in order to fill your end of the contract. If you find your needs are not being met you need to let me know. Working around your schedule, I may ask you to take a trip with me. Do you have a passport? She answered all my questions. She excused herself saying she had to use the rest room. While she was away, I reviewed my interest in her. Beautiful, hot, fuckable, great legs, nice ass. I liked that she looked me in the eye when she was talking. I was thinking to myself, how can I get a free fuck out of this girl, before making a full commitment to her. She could be the best looking babe in the world, but a complete dud in bed. I heard her footsteps returning and looked up. When I first saw her she was wearing a fancy white tee shirt with an obvious bra, supporting her ample tits. She had removed the bra giving me a wonderful view of the outline of her tits, and the dark circles of her puffy nipples. Instead of returning to her seat across from me she slid in beside me on the booth. Her hand went immediately to my upper thigh, sliding up to feel my cock through my pants. Oh this feel nice, she said. I think I can keep this guy happy as she stroked it. The bar was still mostly empty, so I pulled her to me and turned her head so I could kiss her. My other hand went right to her tits. So she said how busy are you? Would you like to come up to my apartment for a free sample. She continued stroking me, and said if you are going to be my only source for sex in the foreseeable future let’s find out if this thing, as she squeezes my cock, can keep my hungry pussy happy.
We walked the three blocks to her apartment as we continued to get to know each other. Mother from Korea, father from Indonesia. Has three brothers, and one sister. Father is a baker, and has a small cake shop in Sacramento. Too many kids to pay for their schooling, so she is loaded up with student loans. Got a job in the school book store to pay the rent. Couldn’t stand the school dorms. Walking with her next to me her tits swaying loose in her tee shirt was a site to behold. She is a Political Science Major. I’m thinking is this a red flag for me I need to find out her politics. Not sure I could deal with a screaming lib. I let it go for now captivated by her bouncing nipples, and what I was going to do with them hopefully in a very short period of time. My fears were answered, when we entered her apartment. She had a MAGA red hat hanging from a hook over a mirror with a American flag decal on it. Great tits, hot body, and a MAGA girl. What else could I ask for. She excused herself saying to help myself to a beer in the fridge. I had a couple of messages I had to answer, as I waited for her to return. I’m a sucker for the color red on woman. When she returned she was wearing a red button down collar shirt open to her belly button. The bottom of the shirt barely covered her pussy and ass. She wasn’t wearing anything else. She did a spin on her toes giving me a better view of her assets. I’m sorry she said I really don’t have any hot sexy negligee, as she stood in front of me. This will do fine I said as I reached in to feel her left tit, and thumb her nipple. My other hand reached around her back to cup her ass pulling her to me. We kissed long and hard swapping tongue as she pushed hers deep into my mouth. Her ass felt perfect in my hand so soft, but firm, as I pulled her into me rubbing my still clothed cock into her. She stepped back reaching for my belt, quickly dropping my pants to the floor, I kicked off my shoes, and she pulled down my shorts to expose my super hard 7” fat cock. Now eye level with it she cupped my balls lifting my cock, and rubbed it all over her face. Licking it from top to bottom, then plunging it deep into her throat. She pulled off of it to say how nice it was, and then took it deep again, fucking her face with my dick. I wanted to hold her head and fuck her mouth, but she was doing such a great job I just stood above her and watched her suck me off. I wanted to run my hands over her wonderful body, as she sucked on me, but she was down so low all I could touch was her head and shoulders. I told her, Babe this isn’t going to take very long before I cum. Giving her warning. I really wanted to see what she would do. I of course wanted her to let me unload in her mouth, and have her swallow my seed. I’ve had woman take in in their mouths, and then let it dribble down onto their tits. That was fine unless I wanted to fuck them after the blow job. It usually required a break in the action, a real mood breaker, as she went off to clean herself up. If they swallow the clean up is taken care of with a tissue. So this was a test she needed to pass. Although some woman could orgasm just having cum on their tits. She was giving me a wonderful blow job, and I was really getting close. I wanted to put my hands behind her head and hold her to me so she couldn’t pull off. So I just rested my hands on her shoulders and hoped she would suck me dry without me forcing her to hold me in her mouth. She could feel I was close, and looked up into my eyes waiting for me to cum. When I did she took it all not letting a drop escape her beautiful soft fuckable mouth. Still holding me in her mouth I felt her swallow my considerable load. She then made a point of slowing pulling off of me and sucking any cum from my cock as she let it pop out of her mouth. She had some cum at the corners of her mouth that she cleaned up with her tongue. So fucking hot. she differently passed the blow job test. After a blow job I usually go oral on the girl, to give myself time to recover. I picked her up, buried my face in her tits, and carried her into her bedroom, placing her seated on the edge of the bed, and dropped to my knees in front of her pussy. I pushed her legs apart, and for the first time got a perfect view of her beautiful pussy, clean shaven except for a small area above her pussy. She was very wet. She sensed that I wanted to eat her, so she used her fingers to pull her lips apart to give me clear access to her clit, and hole. I was very worked up, and needed to slow down. I ran my thumb lightly over her clit, and started kissing the inside of her thighs. Slowing working my way north, teasing her clit with my thumb, collecting her juice and using it to touch her hole, and the length of her pussy. All the time slowing climbing up her thighs with my tongue and soft kisses. Rubbing my thumb on her clit, I had reach her pussy with my face, and blew air on her pussy. She bucked her hips, and lifted off the bed, begging me to help her cum.
I slowly circled her clit that was very red and swollen. She bucked again, and orgasmed. OH Mike she said… I wasn’t done yet, wetting my two fingers off of her pussy, I pushed them into her hole turning them upward hoping to hit her G-spot. At the same time doing a slow suck on her clit. She about broke my nose with another orgasm. Moaning, and cursing F-bombs at the same time. Running her fingers through my hair, holding me in place sucking her clit. She came again, and then had to push me away, not able to handle the intense pleasure. My cock was by now locked and loaded, so I pulled her up onto the bed, flipped her around so she was ass up, and quickly pushed into her. Driving all 7” inches into her in one push, she was so wet. I started to slow fuck her, but she was having none of that as she started rocking her hips forcing me to increase my tempo. More F-bombs, and moaning as I fucked her. Since her blow job, and my orgasm, I was in no hurry, so I was able to just keep pounding her pussy, giving her at least three more orgasms. At least one of them was a full body orgasm that rocked her to her core. She was begging me to finish as she couldn’t take it anymore. I remembered she said at the bar she didn’t do anal. I so much wanted to test out all of her holes, before signing the contract. I stopped pounding into her still buried deep in her cunt, and leaned over to talk into her ear. I told her that I wanted to finish in her ass. It’s up to you. Oh she said I’m afraid. you are so fat. Is that a yes or no I asked? I’m afraid. I will be gentle, you are so wet, there is plenty of lube for me to use. She whispered OK. I pulled out of her cunt, and she came again as I pulled out past her G-spot. I pushed two fingers into her cunt to capture her cum juice, and slowly pushed one finger past her butt hole opening, slowing spreading the lube into her, then pushed a second finger knuckle deep into her working the lube around. Going back to the cunt well to gather more lube. My cock was good and slimy, so I slowly push the head against her anus, and pushed my way in slowing allowing her to adjust to my size. Her moans now were moans of pain and pressure, as I continued to bury myself in her ass. Her tightness was unbelievable. When I had about half way in I slowly pulled almost all the way back out, then slowly back in. Fucking her slowly with only about half of me buried in her. At this point I was worked up with the excitement of being in her ass. I needed to cum, but wanted to get myself deeper in her ass. I stopped and asked her if she was OK? No she said but keep going. I know girls that love this, so I must be missing something. I knew I needed more lube so I pulled all the way out, swabbed my cock up and down her pussy collecting more lube, and not giving her any time to complain pushed back into her. The lube allowed me to go deeper, and I was almost able to bury myself in her. I let her adjust to me, then slowly started fucking her ass. There was plenty of lube so I was able to fuck her without any pain to me. I know if I wasn’t feeling any friction pain she would be OK to. I needed to cum, and increased my depth, and rhythm. I could tell Sunji was starting to get into it, matching my rhythm with her hips, actually pushing back against me. I asked her if she was OK, and she said yes don’t stop, I think I can cum again. I told her I was done and needed to cum, couldn’t hold out anymore. Let it go big boy she said, so I did deep in her ass, Oh god she said I really feel you cuming. I feel every blast. With all the cum in her the the rhythm got easier, and I kept pounding into her. She was building to an anal orgasm that I was hoping she would have. Then at last, as I was softening by the second she shuddered, and came hard. Bucking me almost off of her bent over with me laying on her back. Holy fuck she said as she recovered that was intense. I can see if we are going to do that again we will need to buy some lube. Who knew I could orgasm with a dick up my ass.
The interview seemed to be over well, hot good-looking babe, great tits, great blow job, sweet pussy, and very tight and willing ass. Fucking all three holes as a free sample was a bonus. We showered together and enjoyed soaping each other up. We were both wiped out. I think Sunji had a good time, and kind of got a feel for who I was, and what I expected. Look I said this was great, we should both sleep on this, I do have one other girl who I promised to meet up with. This is a big decision for you to commit to me for the next year and a half till you graduate. I have a personal policy never to make a big money decision until I sleep on it. Oh god she said. You treated me with respect, and I lost count of the orgasms you gave me after 6. I love your big fat cock, and the way you wield it. I will sign your contract and be your slave. Ok I said good to know, Put together your tuition cost, books, rent and I will call you in a day or so. Can you message me your financials tomorrow, so I can take a look at them. Thanks for the free sample it was a great time. My pleasure she said.
About noon time the next day, I was at work, I get a text from Sunji.
“Dear Sugar Bro
I just woke up from your pounding me last night. I have never felt so fully satisfied as I feel right now. Just thinking of your big fat cock is making me wet and drooling. I think your cum is still leaking out of my ass, and oh god is it ever sore.
Your Sugar Pussy:
Sunji”
I had an second interview scheduled with a girl who only sent me two pictures. One of her very impressive naked tits, and one, a close up of her pussy. So unless she arrived at the interview naked I have no idea how I will recognize her. She asked me to meet her at the bar in the Marriott. I told her I couldn’t get there until about 7:00PM. She had my picture so I figured she would find me. I was nursing my brandy when a slightly older woman approached. I’m thinking around 40, very well dressed, very nice build. I tried to compare her breast to the naked pictures she sent me. They looked to be about the same size as the picture. I scrolled to the pussy shot and left it open on my phone. As she got closers she asked if I was Sugar Bro. I nodded my head, and said yes. She was standing right in front of me with her hand already resting on my thigh. I held my phone up to her face with the pussy picture on it. So is this you? Yep she said do you like? Oh I love pussy and your is beautiful. I told her that I wasn’t expecting a cougar. Well she said I was expecting an old fart that I could keep happy, while he funded my education. So I said where do we go from here. Have you had dinner yet she asked. No I said. She explained that the company she worked for had a standing room upstairs, so why don’t we head up to the room and order room service which is amazing here at the Marriott.
She hadn’t yet given me her name, so I said, OK here’s my concern. You haven’t yet even given me your name. I setting here in a 3 thousand dollar suit, wearing a 28 thousand dollar Rolex, and a good size diamond signet ring. You just happen to have a room upstairs, and your looking hot as fuck. Is this a honey trap? I’m thinking what are my chances of getting rolled while your sucking on my cock, and your team comes out of the back room to fuck me up. Oh my God no she said, reaching into her purse. She produced her drivers license, business card that match her license. Her card identified her as a Paralegal for a large Law Firm in the city. A firm that my company used. Her name was Kathy Callahan. She then showed me a wallet picture of her with her 2 teenage kids at the beach. I took her offered license and took a picture of it holding it up in front of her face. So your employer has a room here on retainer? Yes she said. I am responsible for access to the room. Usually high dollar clients, from out of town, horny partners who have a date. And me every once in a while when I want to give it up. I told her I was sending the license picture off to a friend of mine to cover my ass. I could tell she was kind of overwhelmed with my effort to protect myself. Then she said, Ok I understand your concerns. I hope I have made you comfortable. Her hand sliding up my thigh, just pushing up against my cock under the bar. I nodded as I stared down the front of her dress. So what’s on Marriott’s menu, and what’s for desert as I continued to check her out. I’m thinking if I get laid tonight, she would defiantly be the oldest fuck on my long list of pussy. She asked the Bartender to sent up a bottle of champagne to her room, and off we went to the elevators.
In my head I had already settled on Sunji, but Kathy was a whole new way to look at the Sugar Daddy game. If she was as good in bed as I was thinking she would be, maybe I could offer her some help to keep her around. Her tongue was dancing with mine in the elevator as soon as we were alone. Her palm rubbing the front of my pants to feel my cock. She turned her head to whisper in my ear “ I love young meat”. My hand running all over her ass. We hit the room, and continued to swap tongues, breaking the kiss, both of us looking for the menu to order dinner, just then room service arrived with the champagne. We asked him to open it, then he poured into the flutes for us. We gave him our dinner order while he was handy. Once alone we toasted to being unattached, and hurting no one. She kissed me again, and then dropped to her knees in front of me. working on my belt and pants. Let me take care of this before dinner, she said as she took my cock and dipped it in her champagne glass, before sucking me into her throat. She was an expert at giving my cock pleasure. My last orgasm was in Sunji’s ass last night, so I was locked and loaded as she quickly brought me along. I had nothing to do, but watch her suck me to the back of her throat again and again. I warned her that I was close, and she redoubled her effort to get me off. Feeling me shooting into her she pulled me tight to her and let my cum explode in the back of her throat. Slowly sucking me off as she removed me from her soft, warm mouth, licking me clean of any leftover cum. She lifted up her champagne glass and dribbled my cum into the half filled glass of champagne. Swirling it around, then drinking the whole glass down. Kissing my cock head again, and helping me pull my pants up to answer the door for room service with dinner. She ran off to the bathroom as I waited for room service. Well I made it through the blow job without being attacked and robbed. Always a good thing. My evil mind took over, and I was thinking why take on the expense of a girl, when I could score just giving Sugar Daddy try outs. Then I though there had to be a network which would quickly catch up to me, if that’s all I did.
Our dinners arrived, and Kathy emerged from the bathroom wearing only a Marriott white robe. So as we ate she was asking me all kinds of questions about Sugar Daddy. I told her I was new to it, and had never been a Sugar Daddy before. You come to an agreement between two adults, about what is expected. Sugar Daddy pays for this and that. I would expect you to visit my Doc for a monthly birth control shot, and STD testing. In return you would join me for events, dinners, perhaps trips, and satisfy me sexually. Understand I’m a 28 year old man who has a high libido. Do you live with your children I asked. Yes she said. So if I popped in to get my dick sucked or fucked it would be a problem. Yes she said. So I asked how did you see it working for you. When would you be available for any Sugar Daddy? Let alone me. Most Sugar Daddies pick up the apartment rent for the lady, and he visits her apartment. If your kids are teenagers they need you now more then ever. How much is your schooling costing you I asked. $26,000 a year she said. Your taking Law I assume. Yes she said. Do you think your Law firm will keep you on as a Lawyer? Yes I’m pretty sure they will, I’m very well thought of there. That’s assuming I don’t blow the Bar Exam. We continued to eat dinner sitting beside each other on the sofa with our meals on the coffee table. Her robe was untied and every time she moved her tits were peaking out. At one point between bites of dinner, I reached in and pulled on her fully aroused nipple. Oh she moaned, I hope you are not done with me she said. Giving you a blow job has me so horny, I’m ready to do anything to feel that cock between my legs. I gave it to her straight I didn’t see me taking you on as your Sugar Daddy. I’m not sure you will ever find someone to take you on with your present living conditions. Kathy, I don’t want to take advantage of you. Oh god don’t leave, take me I’m your for the evening. I will do anything, just let me cum on your beautiful cock. I pushed the coffee table away with my foot and reached for her. Sliding my hand into the side of her robe, an grabbing a tit pulling her to me. Take me to the bed she said, I want to enjoy this. I scooped her up in my arms and walked her to the bedroom. Pulling the robe off of her as I laid her on the bed. She was so ready. Let me undress you she said as she came off the bed. For a woman with two kids, and a few years older then me she looked really fine. I stood in front of her as she slowly unbuttoned my shirt, kissing her way down my chest as she went lower with the buttons. Pulling the shirt off my arms. leaving a trail of kisses from my neck to my nipples and then doing my left side. I knew that this was her foreplay to satisfy her need. She was in such a frenzy breathing very heavy as she stripped me of my cloths. Once she had me naked, she continued to kiss me all over my body. Finally slipping my cock into her hungry mouth. Then rubbing my cock all over her face and tits. Sucking off the pre-cum that was on the crown. She turned me around and rubbed her tits all over the back of my neck, and then kneeling down to rub them all over my ass cheeks pulling and rolling by balls between my legs with her hand. She was working herself up to a climax just rubbing herself all over me. She climbed back up onto the bed spread eagled herself and said to me “fuck me Sugar Daddy” I put a finger in her pussy and it was soaking wet, she was so ready. I climbed on top and entered her in one motion. Driving all of me deep into her, bumping up against her cervix. Grinding my pelvis into her clit. She came right away, with a full body hard orgasm muffling her screams with her hand. She had sucked me off less then a half hour ago, so I just wanted to pound her for a while before I couldn’t hold back anymore. Fucking her missionary I gave her two more orgasms, then I flipped her over and lifted her butt to fuck her doggie, after a short time of slapping her butt then driving into her she exploded like a bucking bronco when she came. Forcing me to hold on to her hips for balance. She was so wet, I pulled out and lubed my dick by rubbing the length of her pussy. Then with little notice I pushed into her puckered anus. She was so wet, and I was so well lubed I was able to slip right into her butt, deep into her ass. Again more screaming as I started to fuck her butt. Oh god, Oh god, that should hurt, I heard her say, but it feels so good. She matched my rhythm with her hips, and I rode her to another orgasm, as I unloaded my seed deep in her butt. Rope after rope of cum blasted into her. I felt you coming again and again she said. Amazing feeling, it feels so warm. As I was just finishing up and about to pull out she busted another strong orgasm. Oh god she yelled never had an ass fuck orgasm before. That was nice she moaned. We showered together. She was spending the night in the hotel room, and I needed to leave. As I was getting dressed to leave she was sitting there watching me, and I noticed that she was crying. You would have been a perfect Sugar Daddy she said. No I don’t think so I said. Your life style living with, and raising two teenage kids would never have been compatible with my need to pop in for dinner, a blow job, or fuck your brains out several times a week. I would love to see you again. You are a fantastic lover. Next time you get the hotel room give me a call, I’ll see if I can make it work. With that I left her there crying for what could never be.