One of my Sugardaddies is a businessman, and while he doesn’t pay as well as the others, I do this one just for the fun of traveling. He works for a corporation that has locations all across Canada & the US, and about once a month he serves as a liason between offices and visits them.
He doesn’t have a personal assistant, so for these trips they budget him to hire one from a temp agency or by whatever means he can, and they budget a hotel room and food for them too. He knew Kit and she set him up with me to interview for the position while I interviewed him as a potential sugardaddy.
So I get paid legit money (looks good on the tax returns) and get a quick business trip, AND he gives me a little more of his own cash, as well as other perks.
Plus, his favourite thing to do is to buy outfits online that he requires me to wear. He gives me a bag and I put my makeup kit and toys in it, and change into whatever travel outfit or style he wants me in.
In a distant city I get to be as naughty as I want because I know no one is going to see me once I am in his care.
Yesterday, I arrived at his house in a pencilskirt, boots, and blouse. Typical office attire I wear to my other job. I felt pretty and wasn’t even wearing makeup.
He had a bag with some snug clothes to wear, but had one suggestion for my travel outfit.
No underwear. I took off my bra and panties (but kept the stockings) and put on some “bit too sexy for work” makeup and I sucked his dick while we waited for the airport taxi to come get us. In the car, as I got in the car, he fingerbanged me while trying to stay discrete. I was wet the whole flight there.
Once we arrived in the hotel, he told me to go to my room and get super slutty in the long dress in my bag. Again. No bra or panties allowed. He had bought a waist trainer style shaper corset, so that gave me some curves I wasn’t hating!
I entered his room from our connecting door, dark makeup, red lips, hair straight, long dress, fishnet stockings and my “bit too tall for the office” heels on. Then he gave me my surprise. It was a pair of 6 Inch Stiletto Heel Thigh High Stretch Boots that were leather up the front and strappy in the back.
I immediately put them on and noticed he was tying his tie and putting on a jacket. I had dressed for some slutty times, but he was obviously getting ready to go out. I got a little excited at the prospect of going out in an outfit that I had planned on wearing exclusively “in”. But I had gone for a classy high end call girl look, so it worked.
I asked what his plan was. He said he planned on taking me out to dinner for a nice time because he didnt intend to be nice later.
He made every effort to make me feel like I was on display and complimented me to the point of blushing. I felt sexy as hell.
In the elevator, he pointed out that a few times when we were walking or sitting my nipples would slip out of the dress. I told him I knew. He said he didnt expect to get any special treatment or anything just because he brought me out in public.
I was a bit (ok a lot) drunk and told him he could do anything he wanted because he was dressing me, and paying for me. He shyly said he fantasized about me in this very outfit, and him ripping it off me and fucking me roughly.
I told him, “one condition. I get to keep the boots on, no hitting, you still need to wear condoms in whatever hole you are violating, and you just do whatever you want, as hard as you want until you cannot cum on me any more. Deal?”
He was a bit stunned and I was wet. As the elevator door opened some people were entering. I left the elevator as if I didn’t know him. I went to my room door and turned to tell him I was going to freshen up.
I added a bright blue to my eyeshadow, fresh lipstick and gloss, quickly squirted a bit of lube up my ass and entered the room. He asked if I was sure, and I just said, “If I am not screaming ‘pineapple’ just assume you are not fucking me hard enough.
He noted the bottle of Jack Daniels on the dresser and said, “just in case you needed some. Ive had a few shots of courage myself”. I took the bottle and poured a shot. It went down fast and warm. I then decided not to waste any more time and chugged a swig right out of the bottle. That made my head swim a bit.
He came over to me and said my lips looked pretty. I whispered, “dont be nice” and he hesitated, but then grabbed my dress from the loose low cut between my breasts and pulled me toward him. He kissed me, then pushed me on the bed. He tore the dress and the sound of it caught my attention and his as well.
He pulled out his cock and pushed it toward my mouth. I was waiting for it, but didn’t expect him to attempt a deepthroat so I struggled against his raging hard on trying to climb down my throat, hands hard against the back of my head and neck.
My squirming fueled him and he grabbed my head, pushing him in me while I tried to remember how to relax my throat. He climbed over me and fucked my face a few times and it was so raw and merciless that I didn’t even care that I couldn’t breathe. After giving me a chance to catch my breath he did it again.
He pulled out and put on a condom and instinctively my legs went wide. He handed me the JD bottle and I took a hard shudder to shake off the big mouthfuls I forced down.
He grabbed one leg and flung it over so I would roll onto my belly. He held my arms behind me and roughly entered my ass. Like, zero buildup. BANG.
I came. The rush of alcohol, the rough anal and the whole naughty kink of the experience pushed me fast over. I saw white for a second, but he didn’t stop.
He fucked me so hard. I was glad I gooped some lube up there. The pinch had me trying so hard to resist clenching, but it was so good.
He pulled out and snapped the condom off, cumming all up my back and in my ass crack.
He took a breather on the bed. He asked if we had ice. I stood and realized my feet were drunk and took a second to get balance. My ass felt worked. I straightened the dress and pushed my hair flat and said, “Should I go get some” My exhibitionist side was on fire, and he liked showing me off. So I took the chance and strutt down the hall in a dress with a rip in the front and got ice we didnt need.
No one saw me, but I did catch a look at myself in the mirror near the elevators. My makeup smudged, no lipstick to speak of on my lips (but a little smudged around them) and cum down my back.
I came back in the room and he was tugging himself hard again. I put down the ice and he pulled me towards him. He proceeded to find the rip and use it to tear the dress off me. He was NOT gentle.
He fucked my pussy from behind and wasn’t nice about that either. He decided I needed more lipstick and I put it on expertly despite being fucked from behind.
He then proceeded to ruin my lipstick, again throating me. He came on my face and said, “we need more ice”
I said I didn’t have a dress, and he said, “I dont recall asking if you did”
I was a little more hesitant leaving the room with nothing but boots and a faceful of cum. But I mad the fast strutt down the hall. I thought I might have died a bit as I put the card in the door and heard the elevator ding. I was quickly inside.
Two pails of ice on the counter, no Jack Daniels left, and it wasn’t long until I had another load of cum on my face, trying to remember how to breathe.
He dismissed me, a sloppy wreck of drunken sluttiness. He informed me that he set a wake up call for me 20 minutes ahead of when he wanted to get up. He expected me to be clean, fully nude, and cute makeup as I woke him with a blowjob. I agreed and left to take a fast shower while I could still unlace my boots and crashed hard in my own room on a fresh bed.
This morning, as he required I woke him up and sucked his musky cock that smelled of stale cum and my lube. I ate his cum and he smiled warmly at me.
He left me some spending money and told me I could do whatever I needed to do. He didn’t need an assistant for his meetings today, but he wouldn’t mind me swinging by the office for a quickie at lunch. The meetings can get long and boring and he needed something to perk him up.
I visited the office and was looking rather “Mad men” pinup in my offiec attire I travelled in yesterday. I spent some time on my knees
He suggested I find something pretty to wear later. He said tonight would be less rough. I put on a fake pout and he said we would still play.
Now I am wandering the mall in my business outfit with my hooker boots. I am still not wearing a bra or panties. Rules are rules! I have to kill some time before his meetings are done for the day and we can go get something to eat.
snowghoul
pixelskylines
dailybridgerton
