I had previously shared stories of when I was in college and had a sugar daddy. From time to time, he would ‘lend’ me out to friends of his; sometimes he would come along or other times it would be just me and his friend or friends. One friend who joined us frequently was a lady named Anne. She was the same age as my sugar daddy – mid-40s – and her job brought her often into town, and we would almost always play with her.
One summer, my sugar daddy called me and said he was sending me to Boston because Anne was finishing up some international fair and then taking a little break. She invited him and me over so she could relax and have some fun. But since he was busy with work, he sent me ahead and would join us later.
Anne worked in the hospitality industry. Though work is an understatement – she either owned a couple of hotels or was on the board of a company that owned hotels, I don’t remember exactly. I flew by plane and was chauffeured to a hotel she owned and went up to a five-star suite. That Anne had planned for an exciting time was evident – there was a small suitcase of toys; everything from vibrators, dildos, strap-ons, restraints and everything that promised a good time. A small bowl on the bedside table was filled with condoms.
I had the first part of the day to myself, as Anne was still working. I rested up a bit, and then I got a call from her with instructions to go shopping and treat myself to some lingerie. She had left a credit card for me to use, and I was to dress in what I bought. She would be coming that night. It didn’t take long for me to shop, and I found some sexy, hot lingerie that I knew Anne would like.
After I came back to the hotel, I had a light meal, then I went up to the room, took a shower and tried on some of my new lingerie. I chose a dark red babydoll, super thin and soft, completely see-through. I wore only that and heels – no bra and no panties. I looked good if I say so myself. The transparent fabric neatly showed off my firm breasts and round ass. Being busy with college, I had not found the time to get a tan or anything, so my bright white skin looked perfect under the red of the babydoll. The contrast between what was covered by the babydoll and bare skin was pretty eye-catching.
The closer and closer it got to the time Anne was coming, the more excited I got thinking about what she would have me do, and I ended up playing with myself on the bed. I had cummed once when the phone rang. I answered quickly, and Anne was on the other end of the line. She could tell that I had been doing something and had me explain in detail what I had been up to. I told her everything, and she said to me that I had been a naughty girl. That only made me grin like a happy idiot. Then she gave me the bad news – she would be delayed. Anne told me to order a drink from room service. She gave a number for room service – not the number on the little book next to the phone. Anne said that was a unique number for bigwigs like her. Then she told me that since I had been naughty, I had to answer the door in exactly what I was wearing – no covering up in a robe, and I had to invite the guy in and ‘tip’ him. When I asked in a surprised voice, “Tip?” Anne laughed and told me I had to suck him.
I was never much of an exhibitionist, but Anne liked to show me off. If she had been there to tell me what to do, I would have done what she wanted immediately to please her. But doing it just by myself felt weird. I was slow to respond, trying to think of some way to get out of that, suggesting that I could do something else. But Anne did not budge; she cut off my protestations and asked me if I was going to argue. Her voice hardened and took on a commanding tone. I knew better than to argue when she spoke like that. A meek, “No, Mistress,” was not enough to satisfy her. In no uncertain terms, she told me that now I had to do more than just suck the guy off. I had to fuck the guy, and when she came, I should either be wearing the proof or have a full condom for her to inspect.
After Anne hung up, I dithered in calling the number she had given me. Heck, I was so embarrassed by the idea that I did not even know what I would do to entice the guy to come in to give him a tip or how to get proof. Looking back now, given what I read on these subreddits, being dressed the way I was would have been enough. I went to the bedroom, grabbed a handful of condoms, and placed them on the desk in the front room.
Finally, I picked up the phone and dialled the room service number, and ordered a drink to my room. The guy on the other end was very professional – asking the details of how I wanted my drink – it made me even more flustered. When he said, “Right away, ma’am,” I squeaked a thank you and hung up.
Then just a few minutes later, there came a knock on my room door. I waited nervously by the door, and instead of opening it, I asked, “Who is it?” like an idiot. There was a brief pause, then the same voice as the one on the phone answered, “Room service, ma’am, with your drink.”
With no other choice, I opened the door slowly. I peeked through the crack first. The guy was older than I expected – I had thought it would be someone in his twenties or so. But it was a handsome middle-aged man with a smile. “Your order, ma’am.” He said, holding up the tray.
I nervously smiled back at him and backed up, allowing the door to open, asking him to come inside and place it on the coffee table. I was blushing as it was apparent that he could not control his eyes. He was looking up and down at me. Despite my embarrassment, it was gratifying, too, to see him almost gape as he saw my near nakedness.
He walked past me and went to the coffee table, and I closed the door and moved next to the TV and a wooden desk. He placed the drink on the table and turned towards me, his eyes still roving over me. He took a step towards me and handed me the bill and a pen to sign it. I took them from his hand and turned around to place the bill on the desk to sign, still trying to get the words out that I wanted to tip him. I knew I was giving him a good look at my bare back. And even though I did not need to do it, I bent over the desk slightly to sign the bill with some exaggeration on my part by spreading my legs apart, which meant that the short babydoll rose and rewarded him with a clear look at my fully bare ass and pussy.
I took my time to sign the bill. When I turned back, I could see from the look on his face that he had taken a good look and enjoyed the view, though he smoothed his features into a professional smile. My skin flushed even redder, and I felt tongue-tied. He saved me from saying anything by asking if I needed anything else, and that was my opportunity. In probably the world’s sexiest mumble ever, I said, “I have a tip for you.”
His eyebrows rose, and the professional smile on his face was replaced by a leering grin. “A tip, ma’am?” I was surprised that steam was not coming out of my ears. I indicated towards the condoms on the desk next to me. “You can use these.” He glanced from me to what I was pointing towards. He took a step towards me. “And do what?” His voice was no longer professional.
He did not wait for me to answer. He spun me around so that I was facing away from him, he reached over and picked up a condom, and I heard him unzip and tear off the wrapper. I felt him grabbing my waist with both hands, and I felt his hard cock rubbing against my pussy from behind. He started applying force and pushed his cock into my pussy. I was already wet, and he slid into me easily.
He started fucking me, bending over me, his breath hot on my neck. He reached and started playing with my breasts and started rubbing them, pinching my rock-hard nipples with his fingers. His teeth nibbled on my neck.
Despite the earlier embarrassment and nervousness I felt earlier, I started to enjoy feeling him stretch out my pussy. I reached down and started playing with my clit, moaning louder and louder. That seemed to encourage him to go faster and faster. I cummed as he kept pounding me. He kept on fucking me, and seconds later, I felt him thrust deep and cum.
When he finished cumming and got off me, I quickly reached and helped him take the condom off as I wanted my proof. Then I asked him to leave, and he did not seem surprised at all by that and left with a quick thanks. Which surprised me a little since I thought he might have something more to say.
My surprise was answered less than twenty minutes later. Anne came into the room, followed by the room service guy. Except that he was no longer dressed in his uniform. He wore casual clothes, and Anne introduced him to me. It turned out he was a friend of hers, and the two of them had planned the whole thing between them because that was a fantasy of his. And thanked her for having me fuck him. He had been expecting just a blowjob. Anne accepted his thanks and told him that there would be more than enough time for him to enjoy my mouth.
He recounted the whole story to Anne while I sat on her lap, and she fingered me. She told me she was very pleased with my performance, making me cum at least three times with her fingers. He was turned on again watching us, and he fucked me while Anne sat on my face.
Then we ordered actual room service, and she was kind enough not to make me answer the door in the nude. She let me wear a robe this time.
Source: reddit.com/r/gonewildstories/comments/rkruy3/i_ordered_room_service_and_i_got_some_good
That’s a wild story! I’m jealous of your life