(727)563-4084
Oct
14
2019
An Overnight With Carissa
 
It had taken me almost a year to fully make the transition. I finally left the nursing career to focus more on escorting. I enjoyed making my special friends feel wonderful. I now have regular friends who come to see me on a weekly basis. I have confidence in knowing I can put smiles on their faces and being the woman I am, I am confident you may want to make an appointment with me very shortly. I love meeting new friends. I am not prejudice and I love all men. I had taken almost all the steps into my new life but one. I hadn't yet had an overnight booking. The option had been on my website all along but it is expensive. There are also stipulations. I will only consider an overnight from a client if I had seen them before, making sure that we are compatible, I would want a nice high end resort so we can enjoy the pool and Jacuzzi, we both should do activities together, and there would be some sleeping, not all sex. I'm not a machine, I'm a woman and I need my fun and sleep. 

It was a man named Bill who contacted me and requested an overnight outcall appointment. He was a man in his mid fifties who sometimes traveled to my area. He had visited me once and I had also done an outcall to his hotel once. So I knew him and I knew it would be safe. Even so I hesitated at first. Overnight meant 8 hours. Bill had said he wanted us to go to a restaurant first, and then go back to his hotel room, even with the sleeping it was a long time. Could I hold his attention all that time? 

I spoke with  Samantha. Now if you have read the other two parts you'll know who Samantha is, she is my best friend and the woman who helped me get started in escorting. She had done a few overnights so she was perfect to talk to. What she did was ask me a question. Was Bill easy to talk to? I thought back to the times I had seen him. He was easy to talk to and funny. I realized I could cope with being in a room alone with him for eight hours. 

I made the appointment but I had three weeks till Bill would arrive and some of the details would have to be firmed up later. Bill was one of the few married men who spoke openly about being married with me. It was a loveless marriage with separate bedrooms but his wife wouldn't take kindly to him sleeping with another woman. As far as she knew he was under her thumb and only got sex on her terms. Bill would have to make sure that she thought she knew he was somewhere harmless that night. 

The one choice that I took out of Bill's hands was the choice of hotel. I took a recommendation from Samantha and insisted on it. This was a high end resort, which is in Kissimmee.  It has a private Jacuzzi in the room and you don't even have to leave the room.
Of course if you know of a place similar, I would not reject. I just don't entertain overnights in my home or in a crappy area. My safety means a lot to me and I value my safety.

Magicians trick you into thinking you see something that you didn't. It's the same with getting past receptionists. You trick them into thinking they see something they don't. If I were meeting a client in a hotel I would go to reception and ask for him. I would be wearing a business dress, be carrying a briefcase. It's all about presentation. The receptionist see's a businesswoman coming from an office for a meeting with the businessman in room whatever. What they didn't see was my briefcase contained wet wipes, condoms, sex toys and what they defiantly didn't see was that under my business dress I had on sexy lingerie. 

By going to reception I didn't draw attention to myself, as that is what a legitimate person does when they have a meeting. Getting the room number by a phone call and then trying to sneak up to the room with out being noticed will get you noticed. But for overnight I needed to know that the resort was not going to be too nosey. So using one that Samantha had used on a few occasions made sense. Bill was fine with it as well as it was nicer than the hotel he normally stayed in, as he wasn't actually coming to town on business this time but making the trip just to see me, he was paying for the resort himself as well. In fact thinking of what it was costing him just to spend the night with me made me realize I had to exceed his expectations.

The arrangements all went smoothly. Bill was able to book the resort and a restaurant as well as book his plane. For my part I made sure that both Samantha and another friend Sabrina knew where I would be and were expecting text messages from me at certain times. Although I thought Bill was safe I can never trust anyone fully. 

The plan was that he would get to town and check into the resort. I would meet him there then we would go to dinner. That way I'd have the opportunity to drop off my small bag of things I'd need first. After the meal we would retire to the resort for the rest of the night. I would leave at eight the following morning. 

The night before I was a little unsure but I knew that I could cope with it all. I'd had two previous sessions with Bill that had gone fine. I had also been booked for restaurant and function dates by other men and I had been the perfect companion, in fact the only difference between this and a four hour dinner date was that after the two hours in the restaurant and two hours playtime there would still be six hours to go, part of that would be sleeping so I knew I could be on my A game for 8 hours straight. I quickly showered and then put on a set of black lingerie. To this I added sheer black stockings, I also put on a very tight fitting evening dress and a pair of black stilletos. I wore some dark red lipstick and just a touch of eye shadow. 

It was about a hour drive to the resort. As the cab drove on, I let my mind wonder into the night ahead. I told myself that it would be just like a four-hour dinner date except I'd have to go just a little further. I started to realize that the only thing I wasn't sure of was the actual sleeping. Other than that I would be fine. 

I walked into the resort and straight up to the desk. I told the girl behind the desk that I had an appointment with Bill and asked her to tell him that I was here. 

Of course in the early evening, and dressed as I was, my businesswoman coming for a meeting act wouldn't wash. I'm sure that the receptionist had an idea what was really going on. She didn't bat an eyelid however, just as Samantha had told me, and phoned up to his room. Once she replaced the phone she told me the number and said that I could go right up to the fourth floor.

I took the elevator up to the fourth floor and then walked down the corridor to the room and knocked on the door. Bill opened the door and let me in. "Wow you look amazing." He said as he shut the door behind me. "Thank you." I said. Bill looked sexy in his suit.


We chatted a little while I unpacked my bag.  Once I was done with unpacking it was time to go.
When we got to the lobby of the resort I stood near the door as Bill asked the reception desk to call a taxi.  I then took his arm and we got into the taxi.  I got a slack jawed look from the driver as I got into the taxi. The idea was that I wanted to look dangerous and alluring and I was succeeding. 

I'd like to say that the restaurant was great, but it wasn't really. It was expensive and exclusive but it didn't have any soul. The food was good so no problems there.  I was the perfect companion. There is a knack to dinner dates like this. You start off the evening being friendly and chatty but as the meal or function goes on you have to ramp up the tension. Be alluring and dangerous, be a femme fatal and make sure that by the time you are in the taxi on the way to the hotel that the tension can be cut with a knife. 

I was certainly able to ramp up the tension with Bill. By the time the deserts arrived he was starting to stammer a bit and had trouble holding my gaze. I slipped off my left shoe and run the inside of my foot against his leg under the table, as I did he almost dropped his spoon. After Bill had paid the check (which in spite of his and the waiters best effort I could see was three figures) he went to the men's room. This gave me a moment to check in with Samantha and Sabrina. 

Once we were back in the hotel room, having walked past a receptionist who didn't look up from his computer, it was time for me to let all of the tension out. The first thing I was able to do was make the lighting soft and seductive. This was actually easy; the first switch I hit had the desired effect. The second thing was to ask Bill to unzip me. Once I was able to wriggle out of the dress I had a great feeling of power as I let Bill look at me in just my black lingerie and towering stilettos.
"Are you ready for some dirty love?" I said. "Urm." Was all he could stammer. I took that as a yes and stood in front of him and started to push his suit jacket from his shoulders. He got my meaning and took the jacket off. I took it from him and threw it over a chair that was in the corner of the room. I then undid his tie and started on his shirt. I'm really not sure that Bill knew exactly what was happening to him. It was very different from our last meeting, but I was in the mood for playing a role and if I just went through the motions it wouldn't have been special. With out much effort Bill was soon naked in front of me. I moved in close and kissed him deeply. As I did I put my right arm around his shoulders while my left hand gently teased his already hard cock. I moved my lips away from his and moved my arms. Gently pushing him away so that he was sitting on the bed. I took off my shoes and then placed my left leg on the bed as I unclipped the suspenders and gently rolled the stocking down to my knee before I removed it. I repeated this more or less with the right leg. I unclipped the garter belt and threw it over the chair where most of Bill's clothes, my dress and stockings were. Well it wasn't as if we were planning on sitting and watching TV. I took Bill's left hand and gently got him to rise to his feet and then I dropped to my knees in front of him. I again took his length in my hand and gently started to stroke him. Again I was building the tension. I looked up took his gaze with my eyes then I let go of his cock and gently slid him into my mouth. It was a very long and very slow blowjob. I spent a lot of time gently teasing the tip of his cock with my tongue bringing him close to the edge but not quite over the top. My knees were not up to too much kneeling so we soon ended up on the bed, where I was able to continue to use my lips and tongue to keep him at the edge. I started to feel that he was not going to be able to take much more teasing. I shifted position so that I was laying on my side next him. Propping myself up with my right arm while my left hand was wrapped around Bill's very hot and throbbing cock. "I want you to cum for me honey." I said. I started to stroke just using my thumb and forefinger. Gentle long strokes at first and then I tightened my grip and quickened my pace. Bill's breathing started to become heavy. "Just let yourself go darling." I whispered.I wrapped my hand completely around Bill's shaft and gripped tight. As I did Bill's hips bucked off the bed and he ejaculated. Not just a little but a lot. A whole pool of warm cum sprayed over his belly and reached his chest. I kept my grip on him until he started to soften a little and then I let go."That was wonderful, my whole body is tingling." Bill said. I smiled to myself and got off the bed. Before we had gone to the restaurant I had made sure that all the supplies I needed would be close at hand. I picked up a box of wipes from the nightstand. "Just relax for a while. I'll clean you up a little." I said. Being an escort is not all glamour. I took a couple of wipes and mopped up most of the cum from Bill. I then went into the bathroom flushed the wipes and washed my hands. It was time for a change of image so I stripped from my lingerie and put on my silk robe that I'd hung on the back of the door. 

I took a few moments to remove my make up and brush my teeth. I was ready for the night. I went back into the room and Bill was sitting on the edge of the bed. He looked around at me."I feel all tingly I've never had an orgasm like that before." He said."The nights still young, lets see if we can't keep you tingling till morning." I said. Bill stood up and slowly walked to the bathroom. Once he shut the door I was able to sort out the various clothes. I hung my dress in the wardrobe and also hung up Bill's suit. My black stilletoes shoes were wrapped in cloth and put into a special box. For the journey home I had a pair of sneakers. I was also able to text Samantha and Sabrina. I then got myself under the covers of the bed. Although still wearing my robe. Bill came out of the bathroom and I pulled the covers on my right back so he could get into bed as well. Once he was in I gave him a long passionate kiss. I could taste the toothpaste that he used, not something that I normally encountered. I sensed that Bill needed a bit of a rest before some more fun so I let him go and sat back.

We spent around an hour chatting, which was easy. I was always worried that I might run out of things to say when doing longer sessions. But with Bill it was easy to keep the conversation going. Eventually the chat waned a little and we started to cuddle, and then I kissed him deeply. I could feel through my thin robe that Bill's cock was rapidly getting hard again. I threw the covers back and got up onto my knees so that I was straddling Bill's thighs. I had placed a condom in the pocket of my robe and I took this out, carefully removed the foil and gently rolled it down his now fully erect shaft and checked that all was secure. I untied my robe and removed it throwing to towards the chair by the wall. It fell a little short. I shuffled myself forward and then gently lowered myself onto Bill. I sat up for a moment feeling him filling me and then I started to ride him. Slowly.
Gently I increased the pace and then slowed again. I was trying to make it slow and sensual hoping that Bill got the message that this was merely the overture and that the symphony would follow. Now I'd like to say that we changed positions smoothly, but as always it took a little working out. Not least because I took a few seconds to apply some lube to Bill. I then kneeled and leaned forward so that I was parallel to the foot of the bed. Bill was behind me and we were both reflected in the mirror of the dressing table. I reached back and carefully guided Bill back into my pussy. I soon felt him push deep inside me and I felt his belly push against my buttocks and his hands rest lightly around my waist. Bill started to get into a strong rhythm. Slow at first and then a little faster. I looked to my left and could see our reflection. I started to breath a little faster as Bill speeded up. I started to feel a little uncomfortable and leaned forward a little. I felt Bill's grip tighten on my waist and could hear that his breathing was heavy. I pushed back into him a little and as I did he pushed himself deep inside me. I could feel his cock pulsating as he came. After a moment or two Bill put his arms around me and hugged me from behind, while still inside me. I sat up a little and reached back to make sure that the condom stayed in place as I pulled away from him. I had placed tissues on the nightstand and cleaned Bill up a little and wrapped the condom in one and then went into the bathroom and put these in the wastebasket.

When I got back to the main room Bill had rearranged the bed somewhat and was back under the covers. I got in next to him and we kissed. "That was wonderful, you are just amazing Carissa." Bill said. I smiled. "Well thank you." I said. I started to feel a little more relaxed that so far I hadn't come up short, that my first overnight would be a success, although there was still some time to go. Since we had got back to the hotel room the lights had been low but on. Now Bill reached over and turned them off completely. As we snuggled under the covers in the dark I started to feel a little vulnerable. I can't really explain why the darkness had this effect. It didn't take long for Bill to fall asleep; I think that I had worn him out. I didn't sleep well. Every noise and every time that Bill would shift in his sleep woke me. I must have got some sleep as I was woken by the alarm clock at half past six. 

It took me a moment or two to remember where I was and who I was supposed to be. I had to switch back into character right away. Bill was also woken by the alarm and as I looked over at him I could see him lying on his left side looking at me. Trying to get his eyes to focus. "Morning, sleepyhead." I said. Bill smiled and nodded at me. He was clearly not a morning person."I think I know how to get you awake." I said I then shuffled over and wrapped my left arm around Bill and kissed him deeply. It took a few moments before he was returning my kiss. However I was sure that he would soon warm up. I moved my left arm under the covers and soon I was cradling Bill's cock in my hand. He was almost fully erect. "I see not every part of you is half asleep." I whispered in his ear. I rolled over and took a condom from the nightstand and pulled the bedding back. Bill was now lying on his back so I was able to deftly place the condom over him rolling to gently down his shaft and then run my hand up and down a couple of times to make sure that it was secure. 
I rolled over on my back and pulled Bill on top of me. I felt his weight on me restricting my breathing. I felt him gently push himself into me. I pushed my thighs towards him welcoming him deep inside of me. Slowly Bill started to thrust in and out of me. I could feel his weight on me and feel every breath that he took. My own breathing fell into synch with his and I moved with him taking him deep inside with every thrust. His pace sped up a little and his breathing quickened. I started to feel his cock start to throb inside of me. My own breathing in synch with his and then I felt him bear down deep into me as he came. He kissed me gently and lay on top of me motionless not even breathing for a few moments. It was tender, intimate lovemaking and made me fell close to Bill. There are times when it is hard to keep an emotional distance from a client and this was one of those. But I couldn't lose my control. I gently eased Bill from me and taking a couple of tissues from the nightstand I removed the condom and cleaned him up. I went into the bathroom and threw these into the wastebasket. I went back into the room and Bill was lying on his back looking like he was going to sleep some more. I leaned over and kissed him gently. 

"I'm going to have a quick shower then I have to go." I said gently. Bill nodded. I collected my robe and went back into the bathroom.By the time I came out Bill was sitting on the bed and looked like he was ready to get up."It was a wonderful night Carissa. I don't think I can express how happy you have made me." He said. I don't really take compliments well. I always over think them and when I'm given a complement I tend to just smile awkwardly. That is what I did here. Bill stood up."I'll go in the shower now, will you still be here when I get out?" He asked. "Yes I'll wait till you're out of the bathroom." I replied. 

My traveling home outfit was nowhere near as sexy and seductive as what I had been wearing the night before. I put on a much more comfortable bra and panties set and then a pair socks, a simple jersey and pair of black jeans. I also put on a pair of black Adidas sneakers. As much as I love my Louboutins I needed something a little more comfortable. I packed away my dress and robe as well as the various tools of the trade that I had placed around the room. Then sat on the end of the bed. I had only been sitting for a few minutes when Bill came back into the room. His hair wet and with a towel wrapped around his waist. I stood up and walked over to him. "I really do have to go, but I had fun. I hope you did." I said. "Fun is an understatement. It was the perfect night." He replied. I gave him a warm hug and then picked up my bags, opened the door. We said our goodbyes and I closed the door behind me. 

I felt a rush of relief come over me as I realized that I had pulled it off. My first over night had been successful. Although I thought there was room for improvement. I was happy. The reception area was deserted as I walked through it so no knowing glances from anyone. I opened the door and went out onto the street. Feeling the cool morning air on my face. I turned right and saw that on the next corner was a IHOP so I headed in there. I ordered some pancakes for breakfast. Not something that I would normally have but I felt I deserved a treat. I also had a cup of hot chocolate. I sat down and as arranged texted Samantha and Sabrina then started on my breakfast. Through the window I saw Bill leave the hotel and catch a cab. He had told me he had an early flight, I guessed that by lunch time he would be back at home with his wife. Once I finished my breakfast I went outside and was able to find a cab quickly. As I watched the traffic I felt that I had crossed the last line that I would cross in fully becoming an escort.