I’m planning a trip with my sugar daddy for a few weeks from now and it has me reminiscing about a really fun day we had several years ago.
For context, this is the guy from a few of my other stories. My FFM, my naughty alarm clock, and my beach trip story all include him so if you’re interested in knowing about our other adventures, just check my post history!
So, rewind back to when I was freshly 21. I was super excited about finally being legal drinking age and my sugar daddy had big plans for spoiling me. He flew me out to see him for a long weekend and got me first class tickets, set us up in a nice hotel right on the water and it was all expenses paid no matter what I wanted. We ate incredible food all weekend and enjoyed romantic evenings having drinks poolside or overlooking the Gulf of Mexico at sunset. During the days we spent time in the sun and we even had a couples massage. I was on cloud 9 the entire time and he just made sure my every whim was taken care of.
When I woke up on Sunday morning there was a little wrapped gift on the bedside table next to me and I literally squealed with excitement when I noticed it. I sat up in bed and noticed my sugar daddy was already dressed and on the couch watching TV in the 2nd room of our suite but he got up and smiled at me as he came to watch me unwrap his present. He told me “this is something you will wear for me today” and when I finally got it unwrapped I found a Bluetooth remote controlled vibrator that goes in your panties! It was small, discreet, and quiet. It was designed to sit right against my clit and he showed me how it works and set it up to an app on his phone and everything.
He told me to get dressed because we had brunch reservations and about an hour later I was enjoying lobster and after more more than a few mimosas I wondered what else he had in store for me. I noticed his phone on the table and the anticipation of when he’d start using the app was enough to keep me wet and flustered through our entire brunch. At one point, his phone rang with something work related so he excused himself from the table to take the call. I pulled up my own phone to reply to some birthday messages and to check social media and stuff and then I felt it. A light vibration coming from my toy made me freeze and release a little gasp. I set my phone back down on the table and pressed my hands to my thighs as the vibrations slowly intensified. My eyes darted around the room, trying to see where he was. The vibration changed from a constant pressure to more of a slow strobing rhythm and I had to clench my teeth and bite my lip to keep from moaning out in pleasure. The intensity of the moment caught me completely off guard. I was at the whim of this man and he wasn’t even in the room with me!
What felt like 10 minutes later but was probably only moments, I saw him coming back into the dining room, phone in hand and a wide, knowing smile on his face. I was literally speechless as he sat back down and took a long sip of his coffee while locking eyes with me the entire time. He very deliberately set his cup down and tapped his index finger on something on the screen on his phone. Just like that, the vibrations stopped and I let out a breath I didn’t realize I had been holding. I licked my lips anxiously and waited for what was next.
He acted totally nonchalant and went back to talking about the food and asking me if I wanted anything else? I was quite literally speechless and just nodded my head no and he just chuckled to himself as he beckoned the waiter over and paid our bill.
He leaned across the table and told me quietly “you can’t cum unless I say so, understood?” And I simply nodded my head yes this time as we got up and left. The valet brought the car around and we got in. He started driving and told me he was taking me shopping. His left hand on the wheel, his right hand on my thigh, I was already completely soaked through my panties as I wrapped my hands around his forearm and held on tightly. I looked over at him and he just oozed that quiet confidence. He just knew I was 100% his and would always be his and he was 100% right lol.
We got to the mall and headed inside and he proceeded to take me to literally every department store, every shoe store, and every jewelry store in the building! We were there for several hours and I bought a few things here and there but I tried not to overdo it. He rarely tells me no when I want something and he was really going all out on this trip so I tried not to break the bank or take too much advantage of his generosity lol. He also caught me off guard a number of times along the way by reactivating the vibrator when I’d be looking through a rack of items, or trying on a pair of shoes or something. At one point we were at once of the nicer jewelry stores and he had me try on a necklace that I really liked. As I leaned over the glass countertop to get a closer look in the mirror he restarted the vibe, and at one of its higher settings. The sudden sensation caused me to lose my balance and I had to put my hands out to catch myself on the counter. The girl that was working there and helping me out gave me a puzzled look and I’m guessing she thought I was drunk or something lol. I tried to gather myself but I could see my reflection clearly and I was completely flushed in my cheeks and all the way down my neck and chest too. I focused on my breathing and I was just hoping that the vibe was quiet enough that nobody could hear it humming away.
He stepped up behind me and rubbed the small of my back with one hand as he handed his credit card to the girl and told her “we’ll take it and she’ll be wearing it out so there’s no need to wrap it” and she went over to another part of the counter to run the card and get the receipt and stuff. He took his phone out of his pocket and turned the vibe back off as she turned away from us.
As soon as she was out of ear shot he kissed me on the cheek and whispered in my ear “do you want to cum?” And when I looked at him there was a fire in his eyes. He was loving every second of this. I’m admittedly a pretty ruthless tease lol so he was all about the payback! I very intentionally licked my lips and whispered back to him “yes, but I’m gonna make you cum first. There’s something I’ve always wanted to try”. He signed the receipt, we picked up our bags and then I grabbed his hand and started walking quickly to the nearest department store. I took us straight to the women’s section and I literally grabbed the first dress on a hanger that I could. I then proceeded straight to the dressing room and after getting the little hanger thing from the attendant I asked if I could bring my boyfriend in to help me decide on the dress. She said there was nobody else in there so it should be ok.
I lead him to the furthest stall in the back and immediately dropped all my bags and leaned up to kiss him as soon as we had the door closed and locked. He set his things down and kissed me back with so much passion. We’ve always meshed really well with kissing but this was something else entirely! I pushed him back to sit on the little bench and I dropped to my knees. He pulled his phone back out and restarted my toy as I fumbled with his belt and eventually stripped his pants and boxer briefs off. He was already rock hard so I immediately took him in my mouth and coated him from base to tip in my saliva. He leaned forward to run his hands down my back and to pull my blouse up a bit. The back of the door had a full length mirror so I can only guess that he was enjoying the view of my ass and watched my bobbing up and down on his length.
He turned up the vibe to max and set it to a pulsing rhythm and I just melted from it. I laid my cheek on his right thigh as I stroked him with my right hand. I whispered “I can’t take it, I wanted to make you cum first but I need to cum! Please? Can I cum now???” And he chuckled and said “I was just waiting for you to ask permission. Yes. Cum for me” and then he grabbed my head and forced me back on to his cock. I sucked hungrily on him and immediately let myself go over the edge. I’m not really even sure if it was one long orgasm in waves or a bunch of smaller ones strung together but they came in the same rhythm as the pulse of the vibe and I was in heaven. I tried to keep my voice down but all bets are off when I start to cum. I guess I was getting loud because he gripped my head in both hands and murmured “shhhhh” and then proceeded to set the pace and depth himself. I sank into it and didn’t resist at all. I wasn’t cumming anymore but the vibe was still going. I’m usually really sensitive after cumming and I need a moment with no sensations to come down but I was so locked into the moment that I just rolled with it.
Luckily it was maybe a matter of 30 seconds before he was thrusting his hips up as he pulled my head down. He pushed his legs out stiff, threw his head back and absolutely flooded my mouth. To this day I’m still proud that I didn’t spill even one drop. I swallowed and pulled myself up off of him. If there were security cameras in that dressing room, I can’t imagine how we looked at the end. Him half dressed and sprawled out on the bench, my makeup probably running as I knelt before him trying to catch my breath. He picked his head up just a bit to look me in the eye and he said, “I did really like that necklace on you by the way” and we both started laughing.
We collected ourselves and made sure we looked at least somewhat put together. We left the dressing room and I smiled at the attendant and told her I changed my mind on the dress. We left the mall, raced back to the hotel and fucked a couple of times before ordering room service for dinner. Sadly I had to check out the next day and fly back to college but that was definitely a weekend to remember. Who knows, maybe we’ll repeat some public play on our upcoming trip too!
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/pyw14l/shopping_with_my_sugar_daddy_leads_to_dressing/
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