Gypsie – Milf I Forgot Was Sugar Baby
On Friday morning I threw out a few date invitations and a 27-year-old, that was only a low 7 responded the most compliantly. She was so compliant and so easy to deal with over text that I chose her over her much hotter and younger competition. I set my budget to $1000 a month in “gifts” and about that much again in expenses. Meals, hotels, etc. I had in my mind two strategies that could suit my budget. The first strategy was the most exciting and debaucherous. This was finding the youngest and most naïve girls and spending up to $500 on them per date. I just imagined that soft subtle 18-year-old under me with my raw prick deep in their tight young pussy. Oh it makes my neck tingle. The other strategy was someone in their late 20’s who I could get on with as a friend and bang 1-2 times a week.
The second strategy felt the most conducive to my personal goals. Chasing 18 year old’s, even if I was willing to pay, was time and energy consuming. If I could find some pre-wall girl that I liked and respected and was happy to fuck I could focus more on my commitments to family and business. Since my son got sick in September I have really missed the regular sex I can get when I am in countries where my SMV is higher.
Gypsie was obviously in the second category. She responded quickly to texts and agreed to 7pm at Stokehouse bar and restaurant at Southbank, a five-minute walk from my apartment. She didn’t ask any questions about arrangement and it felt much more like a date. I arrived on time and she was already there. She looked much better than her photos and went from low to high seven. She would have cracked an 8 in her younger years. I approached and she gave me a big hug pressing her nice firm boobs into me. OK, this is a good start, I thought.
Over text we had agreed to sit by the river and get to know each other.
“Do you want to get a drink first.” I asked
“Sure.” She replied.
“I should tell you first that I don’t really drink. I will just get a coke.”
“I don’t really drink either.” She said.
“Haha, well let’s just sit by the river as planned.”
I walked her to a seat with a view of the river and treated it like any normal date. To be honest I forgot I was on a sugar date.
“So you live not far?” I asked.
“Yeah. I have a shitty little flat in Greenslopes. But I am hopefully moving soon. I have just applied for a house in Highgate Hill with my cousin. I just need $1200 for the bond. I already have $700.”
This was not at all unexpected and on reflection it was sort of clever of her keeping the date frame, but dropping a hint on how I might help her. I didn’t say anything in relation to it, but instead I just ignored it. It was mostly habit. I have dated so many girls in Asia that hint at me buying them things. I ignore them and fuck them anyway.
The date seemed to go well, but I had no idea if she liked me or was working me. It seemed just like a regular date with a yes girl. She would site very close to me and laugh at all my jokes. Her top was high cut and exposed just an inch of her stomach. Her tanned white skin and feint blonde down of her tummy shone in the evening light. I wanted to fuck her. We had been there for almost an hour so I figured it was time. I invited her to come back and smoke some weed with me. Next time she said.
I was slightly confused. Her whole body language said take me home and fuck me, yet her words said next time. OK, I said as I walked her to her bus. I gave her one more chance before saying goodbye. I could see her feet wanted to follow me, but she remained standing. I kissed her good bye and went home. I had a shower and reflected. Damn, she wanted me to offer her money. I had forgot I was on a sugar date. I would have easily dropped a couple hundred to be smashing her right now. Oh well, more fish in the sea.
Olivia – 19 year Old first time Sugar baby
I thought I would experiment with my initial communication. I was getting a good response rate from my friendly opener “You look nice” but they were dropping off after a bit more chit chat. I suspected that I could improve this by showing I was more serious for an arrangement. I’m not on this site to be a salt daddy. If I was younger and better looking I might be, but I don’t believe there are a high enough percentage of girls on the site I could bang for free, so it’s not worth my time – and I can afford the $.
So after the initial text exchange I messaged Olivia “Do you want to jump straight to pay per meet. Or do you want to get to know me first?”
She replied “Get to know you first” so I got her on Kik and chatted over the next week. From her photos she was brunette, slim, attractive, but not super-hot. She was the girl next door you would fuck in a heartbeat, but wouldn’t turn too many heads. We started to play the questions game and talk a bit about sex, what our fetishes were, when we last had sex, etc. Things were going well, but we were unable to arrange a meet because we were both busy.
I had a day off work and pinged her in the morning. “I’m not working today.”
She replied. “Have we are agreed on payment.”
I replied. “$300. I could book us a hotel in Redcliffe this afternoon.”
She replied “Which hotel. Haha”
I told her to come to my warehouse first and then we would go to the beach or a café, have a chat and then book a hotel. She agreed, but said booking a hotel wasn’t necessary, but she wanted to sleep with me. I figured that was girl code for just “fuck me me.”
She arrived. She was better looking than her pics. Her hair was tied back, she was wearing mini denim shorts and a singlet with a push up bra exposing her fresh and young cleavage. I gave her a hug. She smelt good. This will be fun, I thought. I locked the gate so no customers would come in and took her into my office. I have a bedroom next to my office in my warehouse. I walked her through the office and into my room. I sat on the bed and tried to make small talk. She stood there looking very nervous, but with an expectant look that screamed at me “Just fuck me.”
“I don’t mean to be rude, but do you have the money?” She asked.
I got the $300 out from my draw and handed it to her. She put in in her purse on the bench and walked back over to me sitting on the bed. I pulled her onto my lap and put my arms around her. I fell back and pulled her with me onto the bed.
“You still look nervous.” I said.
“Yes. Maybe we should just get to it.”
“OK. Have you had a sugardaddy before?”
“No. This is my first time. You have done this a lot before haven’t you?”
“We need some music.” I said getting up to play some tunes on my laptop. She got up too and took her shorts off, but leaving her knickers and singlet on.
We met standing and I put my arms around her. She hugged me back.
“Get right too it hey.” I said as I leaned in to kiss her. She kissed me back passionately and we were off and racing. I rubbed her pussy gently through the outside of her undies and then ran my hand up her toned stomach, over her belly button piercing and up to her breasts. I removed my shirt throwing it on the bed and then removed her singlet and bra. Her sweet young tits popped out and I put one in my mouth straight away and gave it a good bite. I underdid my pants and put her hand on top of my slowly growing bulge.
I sat down on the bed pulling her towards me. She assisted me in taking off my pants and underwear and went straight to work on my cock. She handled it like a pro licking up and down the shaft and then giving me the full deep throat. It was good. I lay back on the bed listening to music while she expertly sucked up and down the length of my cock without so much as a glance against her teeth. As good as it was I’m a giver rather than a taker so I pulled her up and lay her down on the bed.
“You have been practicing.” I said.
“Of course.” She said proudly.
I licked over her sweet young body. Up to her large pink nipples and silk white breasts, up to her neck, kissed her soft lips, and then back down. Grazing my beard against her breasts and stomach as I went down I licked her belly and rubbed her inner thigh with my hand. I went down to her panties and licked her crutch. She moaned and arched her back. I moved slowly to the other side breathing heavily through her undies onto her moist pussy. I licked the other side of her crutch and then pulled her panties of. Her pussy was shaved to perfection. It was big with puffy edges like a cookie, but the lips were small – nice and tidy. I licked her crutch again and smelled her pussy. Mmmmmm. I feathered her clit with my tongue, just a glancing lick and then making her wait. I teased her like this for a minute making her wriggle and moan and then latched my mouth hard on her pussy and began licking and sucking for real.
That went well, but I wanted my dick in this sweet young thing. I took the rest of my clothes off so we were both naked and moved up the bed. I lay down beside her and we kissed. I pulled her on top of me and pushed my shaft against her pussy lips. She remained a little rigid not letting her weight fall on me. We kissed passionately and I moved my hand around behind her tail and fingered her. She started to breath heavier into my mouth and let her body relax. I pulled her by her hips and brought her now dripping pussy on top of my hard cock. I slid her up and down the shaft a bit and then pushed in to her. Oh the tight wetness.
I smashed her in all positions until she seemed to get tired and just lay there on her belly while I pummelled her little pussy from behind. I figured she had been pretty compliant so far so why not push my luck. I reached over to my bedside table and grabbed the KY. I squirted a bit on my finger and pressed it into her bum. She just lay there. I pulled out of her pussy and stuck my knob in her now lubricated arse. The end went in. She gasped, well at least she’s still alive, I thought. I pushed gently for a minute until she got looser and then was able to dig deep and smash that tight little freckle. Placing my hand on her head pushing it into the bed I felt my balls about to explode. I held on for as long as I could and then squirted my DNA into her entrails.
I got up, wiped my dick, and passed her a tissue for her leaky bum. I lay back down on the bed. She finished wiping herself and I pulled her over to rest on my shoulder. I like this sugar dating thing, I thought. She got up after 5 minutes and said she had to go. She got dressed. I walked her out to her car and said good bye.
Although fun, it wasn’t really what I was after. I wanted to spend some time getting to know her and all that, make pretend like it was a real date. I could have gotten what I got from her at a brothel – except the blowing in her arse part. I suppose that was good.
Jess – Slap My Face While You Blow in Me.
The next date was a very cute 21-year-old blonde girl I had been talking to online and she had been sharing sexy photos with me. I liked her sexual confidence and how much she liked her body to be so comfortable sharing photos. My favourite was a short video of her in doggy position slowly swaying her arse from side to side so I could see her sweet little cookie shaped pussy. I also liked the fact when I asked her if she had any fetishes she said she liked being tied up and skull fucked.
I decided to experiment with this provider frame and sent her $70 to her Paypal account for her to buy some sexy lingerie. She bought something (or kept the $) and then sent me some more sexy photos wearing the lingerie. I was excited for our date.
We met in the city and I took her to the pool top bar at Next hotel. My reasoning was they have nice toilets there and with the nature of her texts I thought she might be up for a toilet pull. We met outside the hotel. She was attractive and nice, but was also a bit heavier than her pictures. Never mind I was still looking forward to fucking her. We had a drink and got to know each other. I didn’t really like her. She just wasn’t my type, she seemed career driven and shallow, but she was polite and attentive. I was looking forward to skull fucking her. I threw out some mild tests to see if she wanted the skull fucking in the hotel toilet, but decided it wasn’t on.
We finished our drinks and walked along the river to my apartment. We spoke about a range of topics ranging from work and family to our other recent dates. I was interested to probe her to find out more about the sugar dating world. She didn’t give much up except to say that the other guys she had met on the site were arrogant pricks. She asked me how much I was going to pay her. I thought about it for a second and was about to say $200, but then heard these words come out of my mouth. “Nothing. I’m just going to treat you like my slut and do whatever I want to you.”
She stayed silent as we walked along the river at the botanic gardens holding hands. The moon was out and the night was warm. It was very romantic. “Ok” She said. We got back to my apartment and once inside I went to the toilet. When I came out she was lying on the bed with her pants off, legs apart and showing me her pussy. It looked nice, but she was still wearing a shirt and had sweat marks under the arm pits.
“Let’s have a shower first.” I said. She reluctantly agreed. In the shower she was saying “Put your cock in me. I want your cock in me.”
“You have to wait. Suck my cock first.” I said as she went on her knees and I grabbed her head and pushed my cock as deep into her throat as I could. She held strong trying to hold back the gags. I wanted to see if she was all talk. She took to it well.
Once I figured she was clean enough I took her back to the bed, teased her some more. “Fuck me now.” She said. “You have to wait” I replied.
Finally I stuck it in. It was good, but I wanted to come to quick.
“I’m going to come.”
“Where do you want me to come?”
“Wherever you want.”
I let my nut go inside her. She washed, we had a rest for 10 minutes, and then I was ready to go again. I smashed her for a good half an hour more. She talked up a good game of liking rough sex so I wanted to try and outlast her.
“I’m sore.” She said.
“Do you want to stop?” I asked – to be honest I wasn’t sure I was going to come again.
“No. I want you to come. Own that pussy. Treat that pussy like it is yours.”
Fuck someone has issues, I thought as I pounded that tight sore little pink pussy. I felt like I might be able to come soon. She could feel my breath quickening. “Slap my face.” She said
I slapped her across the face hard. She seemed to like it so I grabbed her throat and then slapped her again. Her eyes rolled back in her head. I slapped her one more time and then blew in her again. We washed up. “You should really give me some money.” She said politely. I agreed. I gave her $200 and drove her home.
Sammy – 17-Year-Old Fatty.
7:45 in the evening sitting in my apartment looking out the window and meditating on my thoughts I get a message from Sammy. “wyd”.
I’m not quite sure who it is. I have a look and it was the 17 year old girl from the sugar dating site that had stopped replying to me. She messaged me on Snapchat saying she was only 17, but at least she was legal. I thought it was funny so screen shot it. Snapchat notified her. She got the shits and wouldn’t reply. I gave up – she must have forgiven me.
“Getting stoned and looking out my window LOL” I replied.
“Can I join?” She asked.
We discussed logistics. She was only a 10 minute drive away. She gave me her address and I went to pick her up. I parked at the address and messaged her. I was a bit nervous. Was a girl and a guy about to try and rob me? I looked across the road and vaguely noticed a very overweight girl walking up the driveway of a group of townhouses. I sat back and waited for my date. The overweight girl walked towards my car. Oh fuck. That’s not my date is it? I will just have to tell her as nice as I can that I don’t like big girls. She came to the passenger door and went to open it. It was locked. I opened it for her. She opened the door and sat down in the seat. I said Hi and started driving back to my apartment.
We spoke about general stuff. She was living there in a share house and she was studying legal services at tafe with ambitions of going to uni and studying law. She seemed nice enough. I could see exposed legs and her skin looked nice and smooth. Apart from being so fat she was ok. I was probably going to enjoy it.
We got into my apartment and I prepared some weed for us to vape. We lay on the bed and puffed. I reached my hand over and rubbed her leg. Her skin was very smooth, like silk to touch. I reached my hand up her top moved and my face to hers. She kissed me passionately and I put my hand on her pussy on the outside of her undies. She kissed me harder. “Turn the lights off” she said. I dimmed the lights and took my clothes off. She took hers off and we kissed more. I was enjoying myself. I rubbed her dripping wet pussy. It was nice. I put my finger in and frigged her vigorously. She moaned hard.
I lay back and she went to work on my cock like a fat kid on a cup cake. Well a fat kid on a cock. She gave good head. I thought I was going to cum so pulled her back and hopped in between her big thighs. We kissed and I slipped my cock into her tight fat pussy. It was so wet and so good. I wanted to cum. I pulled out and said. “I’m going to cum. Finish me in your mouth and then I’ll be good to go again in 5 minutes. “ She complied like a good girl, deep throated me, and took my load.
I lay back and we smoked some more weed. 5 minutes later my dick stirred again. I pushed my fingers into her. She was hot and wet. I got on top of her and dug my prick into her. Her pussy felt so good, but it was weird that her stomach was in the way. I looked down at her oversized torso. This was by far the fattest girl I had fucked. It was like I was lying on this big soft pillow of blubber as I was digging into her. It made me feel a bit weird.
I got her on her knees. It slipped in easily. So tight, hot, and wet. This is better. I smashed her for a while until I felt like coming. “Where do you want me to cum?” I asked
“You can come wherever you want.”
“Are you on contraception.”
“Yes. But you can cum in my mouth if you want.”
“No. I’ve already done that. I’ll cum in your pussy.”
I smashed harder and with a grip of her flabby hips I let my nut go and squeezed what I had left into her. I pulled out and lay on the bed. A couple minutes later I got up, washed and dressed.
“You should buy me a Guci bag.” She said.
“How about I book you an Uber?” I replied.
“OK.” She said. I booked an Uber, gave her a small bag of weed. She seemed happy. I walked her to her Uber. That was actually quite fun.
I fucked Sammy again the following week and felt bad. She was just a stupid fat kid. I didn’t like her at all yet I was fucking her. Then I got a text from Jess saying she had chlamydia. Fuck. I should have kept the $200. I got tested and had it too and had to tell Sammy.
I don’t want to do this anymore.