It has been 3 days since I last had intercourse. I was taking a short break and work was keeping me busy. On Monday, as I returned from my business trip, Ben texted me to say that his girlfriend was going out of town and he needed some company on Wednesday night.
Ben is one my sugar daddies. He is divorced and is in his early 40s, but could easily pass off as mid-30s with his youthful looks and fit body. Currently, he is dating an ambitious career woman in her late 20s who doesn’t give him the attention that he needs. From our conversations, I gathered that she tends to emasculate him by being overbearing and makes unreasonable demands.
One of the more important lessons I learnt early on as I ventured into being a sugar baby was to be a good listener. Allowing my “daddy” to release the stressful aspects of his life led to much hotter sex as he would then be able to focus on pleasuring me.
Ben was no different. He took me to extravagant Japanese restaurants (which is my weakness) and would normally spill his beans to me over fine dining and sake. I didn’t mind the company as he was a charming man, full of interesting stories. His witty sarcasm was a delight and I liked that we could be comfortable with each other.
Ben treats me exceptionally well. He has no trouble satisfying my craving for retail therapy. But tonight, there was not going to be any shopping. Whenever he calls me on weeknights, we usually end up in a 5-star hotel. He sounded like he needed his spirits lifted, so I decided to pick out an outfit to cheer him up. I bought this little red dress a couple of weeks ago and did not have a chance to wear it yet. I figured Ben would approve.
After picking me up from my workplace, we drove to a secluded restaurant to avoid the dinner crowd and bad traffic. He was having trouble focusing on the road with my short dress riding up, making my pink thongs almost visible.
Ben was usually in charge of ordering the food, and he truly knew how to pamper me. As he was seated beside me, his left hand was quick to spring into action as he caressed by right thigh as we began small talk. I am glad the red dress worked.
Along with his gentle voice, the stroke of his warm hands was getting me aroused. I invited his caresses by spreading my thighs and gave him a cheeky wink. He continued caress my inner thighs, getting closer to my panties. I grabbed his arm and leaned in towards his ear and let out a soft moan. We were interrupted when the waitress brought our food, but his hand never left my thigh.
I readjusted my dress so that he could get further access to my wet panties. My pink thongs were partially visible with my dress hiked up. He began eating naturally even though he had one hand under my dress. He was playfully circling my clit. I could feel my pussy wetting my panties and I was struggling to focus on eating, but I noticed his mischievous smile has he continued to eat nonchalantly.
I was visibly distracted. So he decided to stop playing with my pussy and removed his fingers but gave a long suck on them to taste my pussy juices. The sight was a huge turn on and we tried to finish our food quickly so that we could proceed to the next part of our agenda.
He quickly paid the bill and we adjourned to a nearby hotel that we had used before. I really liked the comfortable beds here. Ben had texted me earlier that he had a surprise for me. He had already checked in and we went straight up to the room. Upon entering the room, I was presented with the surprise present that he got for me in his last business trip. A brand new sparkly pair of Christian Louboutins! He really has outdone himself today.
But that was not all that he had in store for me. With such an expensive gift, I knew that tonight was going to be a little more exciting than the usual. Ben was not very creative in bed. He was not as good as Jake, but his sexual prowess was above average. His gentle nature was adorable but sometimes, I wished he would be a bit more forceful with me. Perhaps I appeared too fragile to him.
He reached into the paper bag and brought out the second surprise. It was a tiny paper bag but I immediately knew it was a lingerie. I like receiving lingerie. Especially sexy ones. Ben walked closer to me. His eyes were bright, unlike when he just picked me up a couple of hours ago. He was up to no good.
He grabbed me and turned me around. He fondled my breasts from behind and moved my hair aside to kiss my neck. Feeling his warm hands on my breasts and his kisses on my neck was making me horny. Having a new sexy pair of Louboutins helped. He deftly unzipped my dress from behind, leaving his right hand still squeezing my breast. He started kissing my back as he pushed my dress off my shoulders. This was amazingly a huge turn on. My dress dropped to the ground as he unhooked my bra. He quickly pulled it off me and threw it across the room and viciously squeezed my breasts as he continued to kiss and nibble on my back.
I felt the wetness starting to grow on my panties again. The smell of my dried pre-cum from our dinner foreplay was making me extra horny. I could no longer resist. I turned around and started kissing him passionately while he continued to fondle my breasts and nipples. I tried to unbutton his shirt but the buttons were not cooperating. I decided to rip his shirt off.
He was pleasantly surprised and I saw the growing bulge in his pants. I quickly unbuckled his belt and unzipped his pants. After his pants dropped to the ground, he told me to stop as he wanted me to wear my present. I thought he meant the shoes, but he took out a little red underwear from the tiny paper bag. He ordered me to remove my thongs and put the panties that he bought on. I liked how forceful he was when he ordered me. I happily complied.
After putting on the panties, he told me to turn around so that he could admire his new property. He pushed me onto the bed and said he wanted to take a photo of his property (aka me). I don’t like posing for nudes, so he settled for a photo of my butt in my new panties. Damn, it was so sexy. I was feeling so wet and horny just wearing it.
I smiled cheekily at him as I beckoned him over. This “new” Ben was a great turn on and I couldn’t wait to have him. He stopped by to pick up my new heels and again ordered me to put it on. Wow, he wants to fuck me in these heels. I was really swooning by now. I sat up to put on the heels and walked to the mirror to check out my new heels and thongs.
As I was admiring myself, Ben walked up behind me and started fondling my breasts again. I tried to turn around to kiss him but he said “No. I want you to watch as I fuck you from behind”. He bent me over and spread my legs. He pulled down his boxers to reveal his 6-inch dick. He was not big per se, but he had a thick girth.
I was so turned on bent over the mirror as I watched him pull the panties aside and enter me. I supported myself by placing my hands on the mirror as he wasted no time to insert his thick cock inside me. My pussy was so wet that he had no trouble sliding it in and out of me. He grabbed my waist and he pulled my ass towards him as he pounded me from behind. I could see my huge D-cupped tits bouncing with each thrust. Watching my tits bounced back and forth as he thrust his thick cock inside me was driving me wild.
I was much more aroused than I thought. After several minutes of consistent rhythmic banging, I felt my body tense up and had my first orgasm of the night. I usually have only one orgasm when I had sex with Ben. But within 30 minutes into the night, he had already made me cum once. I turned around to kiss him and he was visibly proud of himself.
I pushed him onto the bed and climbed on top of him while still wearing the precious heels that he got me. His dick was rock hard, pointing straight upwards. I peeled aside the sexy panties that he got for me to reveal my shaved pussy. I straddled his lap as I rubbed my wet slit with his entire shaft.
My pussy juices were glistening his thick hard cock even under the dim hotel light. I placed the tip of his penis at the entrance of my love hole. He impatiently grabbed my waist and brought my ass down. I felt his thick cock slide into my tight pussy and let out a loud moan. Damn, I missed his fat cock. He may not be have a long dick, but he really fills up my insides.
I started riding him up and down, with one hand holding onto his chest for balance and the other grabbing my boobs. He was enjoying the amazing view of my bouncing tits as he supported my up and down movement by guiding my waist. Ben was moaning out loud.
“Oh, Hannah… Your pussy feels so good. It’s so fucking tight. I love it when you squeeze my hard dick.”
His dirty talk has definitely improved. His dick felt so good. I continued to grind myself against his pelvic area as his dick was stretching my insides. He grabbed both my boobs with his hands and started squeezing them as he raised his ass to sync with my grinding. My moans were getting louder and louder as he continued to fuck me.
“Oooh baby. Yes… Yes… You’re gonna make me cum again…” I screamed out in ecstasy.
Ben was breathing heavily by now. He sat up and started licking my nipples while squeezing my other breast with his hand. I wrapped my arms around his neck and leaned backwards as I moaned in pleasure. He continued to fuck me as I bounced up and down his dick. It felt like I was hanging on for dear life.
His pace quickened as my moans grew louder. I could feel his squeeze get harder on my breasts and his body tensing up as he groaned my name out loud. It was such a turn on being the object of his pleasure. He started ejaculating into my pussy as he continued to pound me rapidly. Feeling the jet of his cum inside me, I started to cum too. I dug my fingers into his back as I came hard. It was the best orgasm I’ve had with Ben.
He fell back onto the bed after we had both climaxed. I climbed off his tree trunk of a dick and I could feel his cum ooze onto my new panties. I laid beside him and he told me that he wanted me to take off my panties and give it to him for safekeeping.
It feels so hot knowing that he will be taking a sniff off my stained panties when he is without me. I felt a sense of power and superiority, knowing that I could give him something his girlfriend couldn’t. I willingly took of the panties and playfully place it on his nose.
He took a big whiff. As his eyes were covered, I climbed over his head and sat on his face with his cum leaking out of my pussy with both my heels right beside his head. Wearing those sexy heels just made me feel the extra ounce of sexy and made me want to be in control.
I playfully forced his head into my pussy. He happily licked up my cum and my clit. I was becoming horny again. He continued to lick my pussy as I grew increasingly wet. I loved his tongue, though he was not as skillful as Jake.
The pleasure threw me into an uncontrollable trance as I continued to ride his head violently. I continued to grind my pussy against his mouth as his lips lapped up every drop of cum from my pussy. With a loud scream, I started cumming again. I felt woozy after that third orgasm and fell onto the bed exhausted.
Nothing quite makes my juices flow like a sexy pair of new heels and man who is desperate to impress.