To recap, if you’ve not read the first stories, then here’s a bit about us. We met when 17, were engaged when 18 and gave our virginities to each other a few months after getting engaged. We married at 19 and enjoyed the company of other couples, and my wife Carol enjoyed a gangbang whilst we were on holiday abroad. Our jobs were paying well, and life was good until the recession struck. By chance, we met a couple of similar age where the wife was escorting and earning such that they had got out of debt and were now solvent. As we were on the verge of losing our home, we agreed to do the same, and this story picks up after Carol had been hired by the agency.
As for Carol, she is 5’2″ and slim with a 34B, 24, 34 figure, with red shoulder-length hair and was just as pretty as you can imagine. Her tits stood out on their own, being nice and firm; in fact, she could easily go out braless but for her nipples, which you could hang a coat hanger on when aroused! As for me, I was 6′, slim build, and looked presentable, I’d imagine.
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We arrived at the hotel just before 6pm and waited until the manager, John Doyler, was available to book us in, exactly as Jenny had instructed.
“Can I help you?”
“We’re Mr & Mrs Wilson and have a reservation for tonight.”
He looked at us both, smiled and said, “There’s an envelope left here for you, and you’re in room 308,” and handed us the keys with a smile. “Jenny has asked that if you need anything, please ring the desk and ask for me so that I can sort the issue. I’m now on duty until 6am, so please don’t hesitate.”
That confirmed what Jenny had told us about the hotels she used; the managers were on her payroll. Jenny also said that part of their payment was a freebie with the escorts, but this was always set up in advance, and we would know before the arrival of the arrangement, just in case one of them tried it on. Jenny didn’t think it was likely, as they were on a good retainer and the perks kept them satisfied, so spoiling this arrangement would seem a bad idea.
We took the keys and envelope and headed for the lift. Once in the lift, I asked Carol what she thought of the manager; she grinned and said, “Very nice, and look forward to being his perk!”
Once in the room, we opened the envelope which confirmed that she would see Mr Smith at 7pm; he wanted her to dress as a secretary, with stockings and a suspender belt. Then at 9pm Carol was to see Mr Jones, who wanted her to be in a dress with just a thong underneath. The note went on to say that all necessary clothing and shoes were in the wardrobe.
We opened it, and there was a selection of pencil skirts, blouses, dresses, lingerie, and heels, all in various sizes and including Carol’s, so all good on the clothing front. This was all courtesy of John, as Jenny was aware it was unlikely we would have those items with us. We learnt later that all the hotel managers had a selection of clothing which they would put into the wardrobe in advance of the escort’s arrivals.
With barely an hour to get ready, Carol got undressed and went into the bathroom for a shower and emerged with her hair in a ponytail and minimal makeup, which always made her look good against her red hair. She then selected the lingerie and went with black with a red pattern and put the bra, stockings, suspender belt and thong on. Fuck, I was drooling just looking at her. She then put on a white blouse and black pencil skirt with 4″ heels. She looked like a million dollars.
It was now a few minutes to 7pm, so we left the room and made our way to the lift and the 5th floor, where we would find room 511. At exactly 6pm on my watch, I knocked on the door. A smartly dressed man in a business suit of approx. 50 years of age answered, and I said, “Mr Smith?” To which he replied, “You must be Mr & Mrs Wilson.” I nodded yes. “Thank you for bringing such a beautiful woman to me,” took her hand, raised it, and kissed the back of it. He gestured for her to enter, turned to me, and offered his hand, saying he’d see me in one hour’s time. I shook his hand and just said, ‘Yes, will do.’
With that, the door closed, and I walked to the stairs and back down to our room. It was only as I played that back in my mind that I realised I’d shaken his hand as I would if I’d met him in a work situation; it was surreal.
For the next hour, I tried to occupy myself with the radio and/or reading a book but couldn’t, perhaps unsurprisingly, concentrate on either. Just before 8pm, I made my way back to room 511. At exactly 8pm, I knocked on the door, which opened almost immediately. Mr Smith stood back to allow Carol to pass by and then thanked her and me for a most enjoyable hour that he very much hoped to repeat again. He again offered me his hand, and once again we shook hands. Surreal, or what?
Carol walked out of the room looking flushed like she’d been well fucked, a look I knew very well, and followed me back to the lift. Once we were back in the room, I asked her what happened, and she just said she would tell me after her second date, as she needed to eat and have a bath. John had already had a plate of sandwiches and pot of tea delivered, saying he thought we might need these. Whilst she ate, I ran the bath for her.
Carol enjoyed a 20-minute bath and again came out looking stunning with her makeup reapplied and, this time, with her hair shoulder-length but with a hairband pulling her hair back. She then selected a thong and a dress (pastel yellow with flowers) and put this on along with the same heels as before.
Just before 9pm we again left the room and took the lift down to the second floor to find room 206. At the stroke of 9pm, I knocked on the door and repeated the conversation with Mr Smith; it was Mr Jones this time, who was wearing a silk dressing gown. He thanked me for bringing her to him and beckoned Carol into the room, closing the door behind them.
I again made my way back to the room to wait, my concentration being no better. An hour later, I knocked on room 206; the door opened, and a flushed Carol walked out with Mr Jones, saying how much he had enjoyed her company and wanting a repeat next time he was in town.
As we made our way back, I passed on the message from John that if we went down to the bar, he had a cottage pie ready for us and a couple of drinks, all on the house. Carol did, though, have to visit our room first to ‘clean up’, as she put it, and find a pair of knickers to wear. Any description of what went on tonight was going to have to wait as she was starving.
We got down to the bar, and John came over and took our drinks order, saying the food will be along shortly. There were only a few people in the hotel bar, and when John returned with a beer and glass of wine, I said I thought the kitchen had closed. He confirmed this, but as the night manager, he stayed on-site, and his room had a kitchenette, which is where he rustled up the cottage pie.
After eating, we retired to the room where I would learn what happened. We stripped off and got under the covers, and she then told me of her two ‘dates’; these are her words as best as I can recall them.
Mr Smith.
“After you both shook hands (wasn’t expecting that, by the way), he shut the door and went to the desk. There, he handed me a notebook and pencil and indicated I was to sit sideways at the desk. He then sat on the bed and dictated a letter, which I was to read back after he had finished.
Well, I’ve never done shorthand, so I had to scribble as fast as I could, but though accuracy was probably not the point here, but roleplay was. When he’d finished, he asked me to sit on his knee whilst I read the letter back to him. I sat as requested with his left hand around my back and his right hand on the inside of my right thigh; you get the picture.
As I started to read it back, his right hand travelled up the inside of my thigh, and I moved my legs apart to allow him to access my thong, which in a pencil skirt was just about possible. Meanwhile, his left hand undid the zip on the skirt; he undid the button and pulled my blouse out of the skirt. His left hand was now on my bare flesh and moved up to my bra, which he undid very easily. I now had his right hand fingering my pussy through my thong, which was getting wetter by the second, and his left hand snaking round under my arm to massage my left boob.
He asked me to stand up, take a step away from him, let my skirt fall to the floor, remove my blouse and bra and drop them on top after stepping out of the skirt. He then told me to turn away from him, bend over, keeping my legs straight, and pick them up. This forced my legs further apart, and I duly bent over and gathered them up, but as I put my hands on the floor to steady myself.
I looked back between my legs to see him salivating at the sight of my bare butt cheeks and pussy, which was barely covered by my thong. After gathering up my clothes, he gestured for me to put them on the chair and come back to stand between his legs, where he cupped my mound with one hand whilst the other went around behind me to grab my bum cheeks. He massaged both for several minutes before he hooked his thumbs under the thong and slowly pulled it to below my knees, where it fell to the floor. He stood up and asked me to remove his jacket, shirt, and tie, then his trousers and underwear; it was only then I noticed he was barefoot, so I didn’t have to take off his shoes and socks!
He pulled me into him, lifted my chin up and bent down to kiss me; we were soon kissing, tongues and all. We made our way to the bed where I lay down, and he spread my legs so that he could get his mouth to my pussy. His tongue danced all around it, entered me and licked me all the while with one finger inside me. He then slowly came up on the bed, kissing me on my tummy and both boobs before our mouths met once again.
I put my hand down to grab his cock, lined him up, and he slid straight in. We then fucked slowly; he started to speed up until he grew very hard and shot a big load in me. He did, though, keep going until I came a few seconds later.
He rolled off me, turned me onto my front, pulled my legs apart, knelt between them and raised my knees so that he could enter me again with his cock just as hard as the first time. Considering his age, I was impressed with him keeping an erection just after cumming. He held my thighs, and with my face firmly on the bed, he started to fuck me slowly at first but very quickly got into a rhythm and increased his speed. My face was being pushed into the bed almost without mercy as he got faster and harder until I sensed he was close.
He gripped my thighs tighter as he pulled me against him for maximum penetration, and with a grunt, he came again, shooting another load into me. Fuck, I was exhausted even if he wasn’t! After he pulled out, he lay beside me, pulled my lips to his, and kissed me softly and sensually as we lay facing each other. It was only then that I realised that I had been in the room for some 40 minutes, as time seemed to have gone very quickly.
We lay in each other’s arms for another 5 minutes or so, recovering, and I started to fondle his cock, which started to harden again. He rolled me onto my back, got on top and entered me fully once again. This time, though, he slowly fucked me in and out, and I was enjoying the feeling of being penetrated by a cock belonging to someone who, until just under an hour ago, I had not met and didn’t know at all and who was going to pay me for fucking me.
This erotic thought (which it was) increased my juices, and I started to cum again as he increased the tempo, and we came together. He said that you would be along in 5 minutes, so best use the bathroom to clean up. I did and finished just as you knocked on the door. As I left, he gave me a £20 tip.
Mr Jones
Again, I noticed you shook hands with a stranger who was going to fuck me. It seems surreal to say the least, but maybe that’s how this is done. Who knows? Anyway, he asked me in, shut the door and told me to stand in the middle of the room and turn around very slowly so he could admire what he was about to enjoy. I did a slow 360-degree turn, and when I faced him again, he told me to slip the dress off my shoulder and let it fall to the floor. This, of course, left me standing there in heels and a thong only, a view he very definitely liked!
I was then told to throw the dress onto the chair and get on my knees. As I did so, he slipped the dressing gown off his shoulders; it fell to the floor, leaving him standing there naked but with a nice semi on. Another similarly sized cock to yours, maybe just a little shorter but very nice, nonetheless.
He beckoned me to walk on my knees towards him and obviously wanted me to suck his cock, but just as I got to him, he told me to put my hands behind my back, not something we’ve done before and very different doing it that way.
I slowly licked his cock from balls to tip and back down again to his balls, which I spent some time on, licking all around them and taking them into my mouth, then up his shaft to the tip, where I took him into my mouth. Being shorter than yours, I could get all of him in, which he seemed to like, and with his encouragement, bobbed up and down sucking, as I know you like me to do.
I could feel him getting close, and he said he would cum in my mouth and expected me to swallow. Suits me, as you know, I like the taste of cum. He did exactly that and let go with several spurts of cum into my mouth, which I just about swallowed without spilling a drop; that impressed him!
He pulled me to my feet and put his lips to mine, and we kissed passionately with tongues, so he must like the taste of his own cum because there was still plenty in my mouth when I realised what he intended. We went over to the bed where I lay on my back, and he went between my legs, pushing them apart to gain access to my pussy so that his tongue could lick me; he then clamped his mouth over my pussy to suck me.
I did clean up after Mr Smith, so hopefully he didn’t get any leftovers, but as I was enjoying what he was doing, I didn’t really care! His finger then slipped inside me, and he massaged the wall of my pussy with his finger and his thumb, playing with my clit.
After several minutes of this, he started to climb up on top of me, and I put my hand down to grab his cock and guide him to the entrance to my pussy, where I moved it across my lips before allowing him to slide the first few inches in. I moved my hand away and grabbed his bum cheeks, and he took over, going in and out slowly but deeper each time until he was fully in.
Once fully in, he stopped and just lay there without moving for not a long time, but it seemed like a long time. Slowly he started to move in and out and went at the same pace for quite a while before increasing his pace and starting to really pump me until he groaned, pushed in as far as he could, and I held him against me as hard as I could, following which he came very hard, with long spurts of cum hitting the inside of my pussy walls — I thought at one point he was taking a piss; they were so intense. Once done, he rolled off me and pulled me to him, so I laid my head on his chest and threw a leg over his.
We stayed like that for quite a while, and I think he may have dozed a little bit. Checking the clock, I could see we only had 15 minutes left and nudged him to ask if he wanted anything else, and he pulled me on top of him, so I grabbed his hard cock once again and placed it at my pussy entrance and slowly let myself down onto his cock.
I basically sat on him, and my pussy just swallowed his cock completely. I rocked back and forth, getting faster and faster until he started to thrust upwards. I then let him take over as he thrust faster and harder until I heard him grunting once again and he shot another load deep into my pussy.
Once he had finished, I said, ‘Time’s up, as you would be knocking on the door in a couple of minutes. ‘I just about got clean before you arrived, and he gave me a £20 tip, and we went down for dinner.”
As Carol got to the end of telling me all this, I was so hard I just rolled her onto her back and fucked her very hard as she kept saying ‘harder and harder’ until I exploded inside her with as much cum as I can ever remember.
We went home the next morning with £80, being £40 in tips and £40 from her ‘interview’ with Jenny (roughly £400 today) and with another £80 to come in as ‘wages’ from Jenny. We called Jenny when we got home to check in so she could be sure we were ok and, if there were any problems, there weren’t.
Jenny told us that both Mr Smith and Mr Jones were very happy with her visit, and both want to see her again next time they are in town. Although it didn’t exist then, and looking back, it all felt a bit ‘TripAdvisor’ in being marked by the punters!
Carol told Jenny that we were also available this weekend, and with our money issues being what they are, Carol said she wants as many as she could give her over the weekend. Jenny said she would ring Wednesday evening, as before, to confirm any arrangements, and so we started on a journey that lasted just under 3 years.
In the next chapter, I will describe some of the ‘dates’ Carol had over those 3 years.