Diaries of a Male Escort *Updated up to Chapter 2*

Introduction

Hey there, my name’s David, and I’ve been a male escort for a few years now. I wanted to take this opportunity to share with you some of the encounters I’ve had. I hope you enjoy them.

Before I do though, something about me. I’m a 26 year old man, around 5ft 11, and with a slender, but muscular build. My blonde/red hair is kept short and usually spiked, and (unless the lady prefers it) I go clean shaven. My eyes are grey, and I would never dream of describing myself as handsome. In fact average would be a great word to describe me. Average height, average build, just average. My chest is naturally devoid of hair, and I keep my genitals shaved. Speaking of my genitals I’m circumcised and have a cock that is about 7 inches long and an inch and a bit wide – so I’m not in any way huge, but I do have an advantage. I have always been able to keep amazing control of my cock, not only can I hold an orgasm in much longer than most men, but multiple performances are the norm rather than the exception. I keep myself fit, and I’ve never had a lady disappointed in what she’s received.

My day job is a systems development consultant. I travel round the country advising major companies about their software and hardware needs. Modestly speaking I’m good at it, and earn a lot of money. However the money isn’t the best bit of my job. The best bit is the flexibility it affords me. Most of the projects I work on have long deadlines, usually at least a couple of months. This enables me to schedule time to work around my other interests, namely my escort job.

I decided to go into male escorting after reading a story on BBC news about it. The money wasn’t what attracted me, I’ve always been a highly sexed guy, and always wanted to try new things, with new people, and this seemed like the perfect opportunity. So on a bit of a whim, I signed up to an escort service, took a few pics, and posted a bio on the site. Within a month or two I’d had 10 clients, and had enjoyed each one immensely.

You see I’ve never been picky about women, there’s always something attractive about a woman. She can be a twenty-stone behemoth, or a 8 stone sapling, there will be something that turns me on about her. As long as their over 18 and still alive, I’m interested.

After a few months, I decided that it may be better to upgrade to a better package…increase my exposure as it were, but after looking through the packages none of them seemed to serve my need. So relying on my day job skills I created my own website. Putting all my details on it, and making sure I was high up on the Google list I hoped this would get me the exposure I wanted.

To say this worked is an understatement. I usually have at least one client a week, sometimes more than one. Most clients once they’ve had one evening with me come back for more. About six months into my career as a male escort, I decided to keep a diary of my exploits, and publish the best bits, this is the document you have in your hand now.

Before we get into the diary properly, just a few bits of information from the website…mainly here for you to understand how my services work, and why some of the girls respond the way they do!

Fees & Services.

I have 5 different services I offer each with a different rate. All the rates are negotiable, and are usually calculated to include petrol money.

Date – £50

I will meet you at the location of your choosing for a date, starting at 7 and finishing by 10 this is perfect for ladies that need a date for a function or party.

Evening Assignment – £100

This will take place from 7pm till midnight (I can arrive earlier by individual arrangement but it will cost more) and it is suggested you take a look at the locations section of the site for where an appropriate location would be to meet. Simply put I am yours for that period of time. Check out the section on fantasy and roleplay for some ideas!

Night Assignment – £200

Same as the evening assignment, except you get me from 7pm to 7am, a full 12 hour shift!

Party – £30 per person

need some entertainment for a party, then hire a stripper with a difference, for parties of 5 or more females. Location to be agreed in advance but it must be willing to host a stripper. I will strip fully naked at the party, while entertaining you in other ways! But no touching is allowed…for that you need the next option.

Executive Party – £50 per person

The executive party is for those who want a really fun time. Not only do you get the full show from the party option, but touching is not just allowed but actively encouraged, as is sucking and fucking. It is suggested this is hosted in someone’s house, as not many establishments like this kind of hardcore stripping!

Locations

I’m based in Cambridge, but am willing to travel anywhere in the British isles (England, Scotland, Wales, primarily) Anywhere further afield (i.e. Ireland) is negotiated on entirely separate rates. Anywhere in a radius of 200miles (practically all of England and wales, I don’t charge petrol. Anymore than 200miles and petrol is charged at 40p a mile and added to your bill. I use a satnav, and travel the most direct route, if you wish to see the route and verify that it is over 200 miles that is of course fine.

Good Locations to meet

The first rule is, if you are concerned or worried, ask! This is meant to make you feel good about yourself…not bad! That said, here’s some ideas!


Hotel

A hotel is an obvious choice. Space and comfort may be important to you for a satisfying and relaxed experience.

Many hotels offer discounts and special offers for single night bookings as long as they are contacted a few days in advance. The most expensive way to book an hotel room is to leave it to the day before – there will then rarely be a bargain to be found, and you will have to pay the daily room rate.

Choose a hotel that you can afford, and are comfortable in. It is often easiest to meet in a Hotel that has a restaurant, allowing you to get to know me a bit over a meal, before going back to the room.

Your Home

The ultimate choice for you to feel relaxed and in control.

You have the freedom to set the scene, mood and atmosphere. Candles, towels, water and whatever else you want can be easily organized by yourself.

Ground rules (usually established by email) help as always. Let me know whether you want me to knock, or just come right in. What areas of the house am I allowed in, etc, etc.

Your Workplace (or other more public location)

This can work but generally needs some preparation / organizing.

You will need to provide me with a reason to call plus good directions and ensure that we won’t be disturbed!

Sitting at your desk and having me visit could be a very interesting experience for you.

I am of course open to discuss any other locations you have in mind…why don’t you surprise me?

Fantasy/Roleplay situations

I am usually open to any suggestions, and have experience in lots of different fantasy settings so feel free to suggest anything. Safety words, your personal comfort, and my legal liability are always factors, so as always if you’re concerned about anything COMMUNICATE!

With all that over with, on with the diary. Just a final note, each chapter is split up into three basic sections, the initial contact phase, the encounter phase and finally my thoughts on the encounter. Enjoy…

Chapter 1 – Big and Beautiful

Name: Karen

Location: Hereford, Herefordshire

Age: 32

Date of Assignment: 15th April 2007

Hi David,

I’m a thirty-two year old BBW from Hereford that’s not been sexually satisfied for years. I have a very low self-image and need to be told I’m beautiful again. I’ve never tried anything like this before so am very nervous, but would really like to book you for an evening assignment. Hope to hear from you soon, Karen.

Hi Karen,

Thanks for getting in contact with me. A good way to ease yourself into something like this would be to book a hotel room for the night, choosing a hotel with a restaurant, then we could meet for a meal before hand, to allow you a chance to feel more comfortable with me and the situation. Feel free to choose a free date on the calendar, and we’ll take things from there. David.

Hi David,

Thanks for replying, I’ve booked into your calendar the 15th April, and booked a room in the Hereford Travel lodge. There is a restaurant underneath I will be waiting at the bar for you at seven, wearing a black dress. I cannot wait to meet you. Karen xx

I drove up to the Hereford Travel lodge, at around six thirty that evening. It was my usual habit to arrive a little early, and give myself time to prepare. Adjusting my tie, I had chosen a black Hugo Boss suit, white shirt and deep blue tie for this evening, I stepped out the car at 6:50, and entered the restaurant.

I spotted Karen, as soon as I walked through the door. It was one of those restaurants where the bar is a couple of metres long and occupies the area immediately in front of the entrance. She was standing sipping a drink, I guessed it was orange juice. She was tall, only a few inches shorter than me, and truly was a bbw. She was probably a size 18, and had huge boobs. Her dress was cut low, and showed amazing cleavage, as well as as the stockinged legs below the knee. I realized that the 2inch heels had probably made her look taller than she was. She had long brunette hair, a little curly at the ends, and a very pretty face, I felt an immediate tug in my pants, performance was not going to be a problem tonight.

I immediately grinned gently and stepped over to her, offering my hand as I said,  "Good Evening, you must be Karen? "

She smiled back a little shyly, and after a brief manoeuver swapping her drink to her left hand, she took my hand and shook it tentatively,  "Hi David, how was your journey. "

I shrugged, and made a so-so gesture,  "Good but the traffic around Hereford wasn’t fun! "

She smiled more fully,  "It never is. "

I ordered a drink, and after a couple of minutes of small talk, a waiter approached and led us to our table.

We sat down opposite each other, I made sure that we kept making eye contact, and smiling reassuringly every time I did so. The waiter quickly took our order, and our wine choice, and disappeared professionally.

 "So what do you do for a living? " I asked, hoping to get the ball rolling. It did, and she was soon relaxing in my presence and chatting idly about the things people chat about. It wasn’t long before our starter had arrived, and left again. Our main meal followed shortly afterwards. Halfway through the mains, and after we had both finished a glass of red, there was a slight pause before she said.

 "So I wasn’t sure about this but I bought a bottle with me, and a couple of glasses, I thought they may be useful in the room? "

I smiled once more at her, again wondering how this pretty woman could be so starved of sex.  "That sounds like a great idea "

She smiled back  "Great, I have to tell you, your making this very easy for me! "

I laughed slightly,  "That’s the plan. "

The waiter arrived just then to take our main plates away, and doing so he asked whether we would like the dessert menu. I laid my hand on hers, and turned to the waiter, shaking my head. As he turned away, I Whispered,  "I plan on having my dessert in the room. "

She blushed fetchingly, and took a sip of her drink, but I could tell she was pleased.

The waiter returned with the bill and after settling it, we both rose, and taking me by the hand we walked outside, and then into the Travel lodge. One of the reasons I like using Travel lodge’s is that they rarely have people on the desk, it’s easy to get in!

This was the case here, and we quickly walked past the desk and along the corridor to room 17. Sliding the keycard in and out, Karen opened the door, and we stepped in.

Closing the door behind me I smiled at her as she let slip her purse to the floor.  "Um so what now? " she queried. All the nervousness was back, now we were getting down to it.

 "How about that wine? " I asked

She let out a breath and turned around, taking the wine out of the mini fridge, giving me an opportunity to stare at that dress covered ass. When she straightened up she poured two glasses and handed one to me.

I motioned for her to sit down on the edge of the bed, and i sat next to her as we sipped wine. Putting my hand on her knee, I slowly stroked up and down her thigh over the dress. She sighed gently, and took a longer deeper sip of wine. Slowly I slid my hand down so that it was on her stockinged knee, then sliding it back up again, this time under her dress, stroking her thigh, until I reached the point her stocking finished and her flesh began.

As soon as my hand hit her flesh, her breathing deepened, Putting down my wine glass, and taking hers and setting it down also, I leaned in and kissed her gently on the mouth. She immediately opened her mouth, and taking the invitation I slid my tongue in to meet hers. We kissed urgently for a few minutes before I broke it off, and cupping her face said,  "You are so pretty Karen. " I removed my hand from her dress, and reached up and cupped her magnificent breasts as I dove in again to renew our kiss. Her hands flew to my chest, and was pressing against me urgently. I broke the kiss once more and stood, drawing her up with me. Then gently kissing her once more I took a few steps backwards.

I slowly removed my jacket and placed it on a chair. I was guessing slow and erotic was the order of the day for this lady. Next my tie was loosened, then removed, and I could see she was getting more turned on by the moment. I started to unbutton my shirt, stopping when I reached the last one. The smiling at her,  "I can’t seem to get this one, could you give me a hand? " She willing stepped forward and quickly unbuttoned the last button, before sliding her hands up my bare chest, and outwards to slide my shirt off.

I brushed her hair away from her face and kissed her again, before easing the straps of her dress off her shoulders. The dress didn’t require anymore encouragement and it slid to the floor. She was a big girl no mistake, but the fat around the tummy didn’t even register, those gorgeous big tits were encased in soft white silk, with matching panties. I cupped the right one again, whispering,  "I can’t wait to see how big the nipples are. "


Karen sighed deeply, her panties now noticeably damp. I kissed her again, then stood back from her as I eased my belt off, and undid the button, that allowed my trousers to fall.

This time it wasn’t a sigh, it was a definite moan, as she saw my cock bulging in my tight boxers. I glanced down,  "Think you can handle the rest? "

She didn’t bother to reply just dropped to her knees, and undid the little button on the slit in the front. She reached in and grabbed my meat, pulling it through the hole. She moaned again as she started to wank me off, slowly at first, before going faster and faster. I groaned slightly, then put my hand on the back of her head guiding her to my meat. She willingly leaned in and stuck her tongue out to lick the top of my head. I groaned again, and she continued to tease me with her tongue.  "Suck it, " I grunted, and she complied. Opening her mouth wide she slid me in an inch or two, then slowly drew me back out. Then as slow as she could she started to piston me slowly taking more and more in every pass.

I took a firmer hold of her head and started to regulate her speed, before long I was fucking her pretty face. Then after a few minutes of an amazing blow job, I pulled out, and brought her to her feet.  "Was it OK? " she questioned. I just smiled and said,  "Phenomenal. But it’s your turn now. " I moved my cock back in my boxers, then dropped them to the floor. I turned her round so her back was towards me, and gazed at that beautiful fat ass. Slowly I ran my hands over her flesh, causing her to shiver in delight. Then pulling her too me, my cock pressed against her ass, I ran my hands over her fat stomach, and to her tits.

She moaned again, and I slid my hands into her bra, and pulled it down, freeing those beauties. Quickly taking one in each hand, I massaged them making her moan even more, before moving my hands to her nipples. I was right they were huge, the aerole were a couple of inches in diameter, and the nipples themselves were hard and erect, easily half an inch across. I started to tease and pinch at those nipples, and Karen moaned deeply again,  "Uhh David " she managed to groan out, before I tweaked one extra hard.

I made sure my cock was rubbing against her ass as I continued to play with those nipples, kissing the back of her neck as I did so. Then just as her moans started to reach fever pitch, I took my left hand away from her tit, and slid it straight into her panties. Delving through the forest of hair I found there, I quickly reached her pussy. She was soaking wet already, not wanting to stand on ceremony, I slid a finger straight in. She climaxed instantly, my finger got covered in cum, as she let out a moan i thought would be heard throughout the hotel.

 "uh that’s so good " she moaned, as i slowly drew my finger out, and moved it to her clit. I circled it for a while, as she got her energy back, kissing her gently on the neck, as her clit and tit were fondled by me. When I thought she had recovered enough, I withdrew my hand and motioned her to sit on the edge of the bed. Her eyes were wild with desire as I took hold of her panties and slid them off, exposing that hairy pussy to me. I grabbed her ankles knocking those high heels off making her stockings the only piece of clothing left to her, and spread her legs, before running my hands down them towards her treasure chest. Spreading her pussy lips wide, as her breathing increased in anticipation, I lowered my head.

She practically screamed at the first lick of my tongue on her clit. Then grabbing my head with both hands she lay flat on the bed, and pushed me deeper into her pussy. I went at it with a will. First her slit, then her clit, then back down her slit again, my tongue ravaged her pussy, until even her moans were drowned out by her need to get oxygen into her body. I could just about see her rubbing her own tits as I ate that pussy. We stayed in that position at least ten minutes, with her cuming twice more, drenching my mouth in her sticky liquid.

Eventually I raised my head, and stood. Still in between her legs, I reached for my trouser pockets, where I knew a condom was located. I unwrapped it, and slid it on. Her eyes were glazed but she knew exactly what was about to happen,  "Fuck me David, Fuck me hard. " she only whispered it, I needed no more encouragement.

I bent my knees slightly and aimed my cock at her by now well lubricated entrance. I slid in like a dream, her pussy, while not tight, felt amazing, and I just luxuriated in that feeling for a moment, before an agonized grunt of desire from Karen brought me back to my senses.

Straight away I started to move my hips, sliding my cock in and out of her pussy. I took it slowly at first, not wanting to hurt her after who knows how many years of neglect. I thrust inside her, increasing my depth with each stroke until I was ball deep inside her. She groaned again, she sounded like she was hyperventilating. I sped up, knowing she could take it, soon I was pounding her pussy hard. My hands grabbed her ankles and pulled them back hard every time I thrust in, taking her as deep as I could.

 "You like this Karen. " i breathed to her,

 "Fuck Yes! " she managed to get out, just as I slammed inside her once again. I moved my left hand from her ankle, dropping her leg over the edge of the bed, and grabbed at her huge tit, and squeezing it roughly, eliciting another groan from her. I rammed in again penetrating that gorgeous pussy like no one else had in years, but this time instead of sliding back out again, I held it deep within her and started rotating my hips, moving my cock inside her. I moved my hand to her nipple, pulling and twisting it as I grinded into her pussy. I watched that pretty face as I fucked her, her eyes were tight shut, and her mouth open, struggling to get the breath in. Slowly I drew my cock out until it popped out of her cunt. Then I gently moved it with my hand, rubbing over her protruding clit, while pinching her fat nipple.

 "Fuck don’t tease me " she groaned,  "Fuck me properly with that amazing cock. "

I drew it out a little longer, my cock head rubbing on her clit, before I rammed it deep inside her.  "Uhhhhh " she cried,  "I’m cummmmmmiiiinnnnggggg! " I felt her cum explode around my cock, and I immediately started grinding again trying to draw out her orgasm as long as possible. It worked, the moan continued, as I picked up her ankles and lifted them as high as I could. This was more difficult than it sounds. I’m not the strongest guy, and these legs were thick. Once I got them high I bounced slightly on the balls of my feet, sawing my cock up and down inside her by now soaked pussy.

Eventually as Karen’s moaning subsided, and her breathing came back under control, I allowed her legs to drop slowly, and brought my cock out of her pussy. Reaching out I brought her back to a sitting position. Her hand automatically went to my cock, and slowly wanked it, enjoying the feel of my well lubricated cock. I kissed her deeply, enjoying the taste of her lips. When I broke the kiss, she stared at me with lust filled eyes… "Do you want me to blow you again baby? " she asked.

I smiled at her,  "Not yet, I want to fuck that beautiful body doggy style first! " The look in her eyes was worth it all.

 "You want to fuck me again? " she asked, she was obviously having trouble believing that this guy she had paid for an evenings work, was taking so much pleasure out of his job.

I grabbed a tit in my hand again and massaged it roughly, looking deep in her eyes I replied,  "If you have the energy I want to fuck you until our time is up. "

Her chest heaved as her breath deepened,  "But I…I was hoping you’d cum in my mouth? "

I took hold of the hand that was still slowly wanking me, and increased it’s pace a little,  "Whatever you want goes tonight Karen, I’m here to please you as much as you can take. So I’d love to cum in your mouth if that’s what will please you, you’ve just got a choice, do you want me to cum soon, and have a short rest before I’m ready to go again. Or do you want to spend all night shagging, and have me cum in your mouth as the climax of the evening? "

Her eyes widened, and she stood, turned, and climbed back on the bed, kneeling on her hands and knees, giving me an amazing view of her full moon. Ass, and dripping wet pussy ready for just for me.  "Fuck me then, I love the feel of your cock inside me, fuck me as hard as you can, and I promise when you’re ready to cum, I’ll give you the best titfuck you’ve ever had before you cum in my mouth. "

I got on the bed next to her and started running my hands over her ass.  "Have you ever been fucked standing up Karen? " I asked her. She shook her head…eyes wide. I got down from the bed and beckoned her over. She followed, her thick stomach wobbling slightly. I kissed her again, and led her over to the desk that inhabits every Travel lodge room. Moving the chair to the side, I placed her hands on the desk, instructing her to bend slightly. Then I moved behind her, that gorgeous fat ass trembling slightly in anticipation. I rubbed her ass, gently at first, before more roughly, squeezing and pulling at the flesh as I rubbed my cock making sure I was still nice and hard. Then taking my cock head I rubbed it down her slit, from her asscrack to her clit, then all the way back up again, teasing her pussy with my bell-end. She moaned, her pussy already wet, was juicing up again, and her breathing was deepening by the moment, She looked over her shoulder, and whispered,  "Wait! I want to feel every bit of your cock inside me, I’m on the pill…please fuck me bareback, I want to feel it. "

I had to check,  "You don’t want me to wear a condom? "

 "No I want to feel it. " she replied looking straight at me.

This was an invitation I couldn’t refuse, I quickly removed the condom. Then rubbing my hands up her stocking clad legs, I spread her but wide, seeing her beautiful crack and pussy in all it’s glory. Taking my cock I moved it towards her entrance, but soon realized that she wasn’t quite tall enough to make it comfortable. Quickly looking round I realized she had taken off her shoes. Smiling I moved towards those two inch heels, then lifting one leg, than the other, placing the shoes on her, and elevating her the necessary height.


 "I’ve never fucked with high heels on? " She joked,  "I feel like a porn star. "

I smiled back and positioned my cock at her entrance.  "Trust me " I said,  "You won’t have to fake a thing ", as I said this last, I rammed my cock back in as deep as could go, the angle meaning I got in deeper than I had ever done in missionary. This time it wasn’t a moan, it was a full fledged shout of delight. I started immediately started to piston in and out at full speed, fucking her pussy as hard as I could. Grabbing the flesh of her ass to support myself I threw myself into the fuck pounding in and out of her cunt. Her head drooped as she started grunting, and panting in turn. Not going to take that on one of my inward strokes I took my hand of her ass and grabbed a handhold of hair pulling her head back as I pulled out and bored back in again.

She screamed again, as I resumed my pace, while holding her head up by her hair. I started spanking that ass as I fucked her. My balls slapped against her clit as I was fucking her, stimulating her even more. I can’t imagine what the people in the next door rooms were thinking hearing these guttural moans, grunts and screams, and now the staccato sound of an ass being slapped.

I could tell Karen’s orgasm was building again, so I put in a final bit of effort, dropping her hair and letting her head sink again, I took hold of her prominent love handles and started to give it all I had, drawing all the way out and penetrating all the way in on every stroke. Before long her legs, then her ass, then her whole body started quivering as the orgasm took hold. I was struggling myself to hold on but exerted my control, to make sure the only cum she took was down her throat.

Eventually her resolve broke and with a shout, her pussy exploded around my cock. As soon as she did her legs buckled, and I quickly withdrew my cock and let her sink to the floor. Her breathing was ragged and her eyes were glazed as she dripped cum all over the carpet. I slowly removed the condom and rested one hand on her shoulder, and one hand massaged her tit as she regained her energy. Finally she looked up at me and said,  "I don’t think I could handle anymore, you’ve worn me out, let me taste your cum. "

I guided her hand to me rod,  "It’s all yours baby. "

She grabbed one of the pillows, dumping it on the ground by me, and knelt I spread my legs, trying to give me a secure base. She sat up as tall as she could as she wanked my soaked cock slowly. She gazed up into my eyes and said,  "I’ve never tasted myself on a cock, do I taste good? "

I pulled her mussed hair away from her eyes,  "Not only do you look good, not only are you a great fuck, but you taste amazing. " Positive reinforcement was why she had paid for my services so I was going to give her all she wanted.

She smiled happily at me, the blush long gone now, and slowly she took the cum soaked head of my cock and slid it into her mouth. She swirled her tongue around it, before taking it deeper a few strokes, obviously trying to get a good taste of her own juices. Then she drew it out again, with wide eyes.  "You’re right I do taste good…I prefer the lollipop to the flavouring though! " Then taking my cock she moved it between her tits, wrapping those gorgeous melons around my shaft, before moving her whole body up and down, wanking my cock with her tits.

We both stared intently for a moment, of the beautiful sight of my cock head appearing and disappearing into a hollow between mounds of stunning tit flesh. Then Karen extended her tongue so that every time my head popped out of it’s breast embrace her tongue played over my head. This drove me wild, and placing my hands on her shoulders I stopped her movement, so that I could fuck her tits myself. Again rising and falling on the balls of my feet I fucked those tits nice and hard. Allowing my cock to penetrate enough to touch her lips each time, then falling into the fleshy embrace once more.

This triggered Karen’s dirty talk, this trait had been mostly hidden, her not having enough breath to manage it probably contributed. But now she went at it with abandon.


 "Yeah fuck them, fuck my big fat tits, fuck them hard with your gorgeous cock, I want to feel it sliding between my boobs. Uhhhhrrrggggh I love the feeling of your legs and stomach on my nipples. " and much more.

And I couldn’t help but agree with her, those big nipples dragging up and down my body was causing me serious problems with losing control. So taking her head in my hands I said,  "I’m ready for you to have a taste Karen. "

She looked deep in my eyes once more… "I’m glad, I can’t wait to taste your cum. "

She repositioned herself, letting my cock fall from it’s heavenly prison. Then pulling it down so it was level with her mouth. Then opening as wide as she could she slid her head down my cock, managing to get a good five inches in on her first pass. Slowly she drew it out again, before moving back down on me, trying to take me deeper. For all that she was a big girl, and her face, though pretty was not small, she didn’t seem to be able to get much more than six inches of my seven in, but I wasn’t going to let that get to me.

I started to roll and buck my hips, making my cock move in her mouth as she continued to pleasure me. She rolled her lips back and let her teeth drag lightly against my cock flesh. I moaned gently, and let my head loll, as she expertly sucked my member. She may not have had sex for a while, but once you learn to ride, you can always ride. She began to speed up her sucking. I held her hair back so it didn’t get in the way and so I could see that beautiful face fucking my cock. Both her hands move from my cock to my ass and she clenched it hard digging her nails in and she tried to force more and more of my cock into her mouth. I knew my orgasm was building, so I relaxed all control, and allowed her to suck my cock how she wanted it. It didn’t take much longer, I could feel my cum about ready to explode, so after a couple more sucks, I took hold of her head and slid it down as deep as it would go on my cock, and just made little motions in her mouth. A few seconds later, a deep guttural groan built in my balls, up through my stomach, and chest and finally burst out of my mouth, as my cum exploded into hers. I held her face in place as she urgently swallowed, trying to drink load I’d just shot into her. Eventually her grip on my ass lightened, and I removed my hands from her head. Slowly drawing her face off my now limp cock, she smiled up at me, pausing to wipe the small amount of cum, that had spilled out of her mouth. I thanked her, then glanced at the clock, it showed 11:30, perfect timing. I smiled at her and said,  "Our time is nearly up Karen. I just want to thank you for an amazing evening, and you’ve got about ten minutes before I need to start getting dressed again. "

She looked thoughtful for a moment, then said,  "You’ve done so much already, just take me in your arms tell me how beautiful I am and kiss me. " I drew her up and into me, holding her close as I could, my arms barely reaching round her. Bending slightly I locked lips with her frenching her vigorously until we broke for breath, then whispering I said,  "You are stunning Karen, you have an amazing ass, beautiful huge tits, and the prettiest face I’ve fucked in ages. I’ve enjoyed every second fucking you, and would love to have the opportunity to take you again. "

She sighed, and smiled, and whispered  "Thank-you "

I gathered up my clothes and dressed, opting not to bother with the tie, stuffing it in my jacket instead. She reached for her purse and pulled out the cash, handing it to me with a hint of embarrassment. I smiled and thanked her and told her not to think of the money, but concentrate on the experience she’d just had. She smiled again, more confidently this time.

Finally just before I left, I gave her a card. This card gets given to all first time clients, it includes a special log on to my website, where they can re-book me anytime. Returning clients always get a slight discount, and those that book more than ten times, receive sizable discounts.

I smiled once more, and kissed her gently, before leaving, at just before twelve.

A day or two later I received this email:

Hi David,

I just wanted to thank-you again for an amazing experience last week. I’ve never been fucked that well in my life, and since my husband divorced me (he divorced me because he felt I was too fat) I’ve put on a lot of weight, and never really thought I’d get to have sex again, let alone enjoy it. Yet for a modest sum, not only were you willing to give me an amazing night of sex, but give me the confidence that I am still attractive and could still find a man of my own, that appreciates me. Don’t worry though I’ll definitely make another booking! With Love Karen xxxxx

And she wasn’t joking, she made another booking for a couple of weeks away, and now she is one of my most regular clients, always booking an evening assignment, about once every month and a half. The sex is always similar, she has never been very adventurous in that regard, but it is always a rewarding evening for us both. We’ve met in hotels, and in her house, and she especially enjoys being fucked standing up in various rooms of her house. I’ve never understood why guys avoid fat girls, they are desperately horny most of them, and all they need is a little encouragement. If you don’t find them that attractive…all that means is that you’ll last longer, and they’ll appreciate you even more.

Chapter 2 – Vintage Wine

Name: Tracey

Location: Braintree, Essex

Age: 56

Date of Assignment: 23rd June 2007

Hi David,

I have a problem, I’m a 56 year old lady that gets little or no service from my husband. He has an important job and is often away, but that is not the problem, the problem is that he has had a succession of very attractive young secretaries (which I’m sure he has spent time with outside of work) and as a result no longer finds me attractive. I’ve tried to keep trim and attractive but age takes it’s inevitable toll. I feel that the best thing to do is to take my revenge by fucking a young stud like yourself in our marital bed while he is on a business trip. I am a very horny lady and cannot wait to be sexed up by you. I have checked and see that you are free on the 23rd June so would like to book you for a Night Assignment. Please come to my home <address blanked out for privacy> and ring the door bell. I cannot wait to feel your young hard cock inside me. Tracey.

Tracey was a true Essex girl born and raised in braintree just an hour away from where I live in Cambridge. I decided to go more casual for this appointment, wearing jeans and a tee-shirt. The air was cool for June, but not cold. I drove up, and as usual in my visits to someone’s home, made sure I was quite early, so that I could drive by the address to see the lie of the land. Tracey lived in a fairly modern semi-detached house, that was clearly visible from the road, there was also plenty of parking outside for my car. I drive a KIA Carens, which not only gives me a great ride, and a reliable car, but also gives me plenty of space in the back…for…well for a great ride I guess!

I drove round a bit before returning to the street just before seven. Parking up, I exited the car and approached the door way, ringing the bell.

Tracey answered the door quickly. Pulling it back, immediately her eyes widened appreciatively,  "David, come on in. " I followed her into her hallway as I took stock of what was to come.

Tracey certainly looked her age, a good three or four inches shorter than me with dark brown fairly short wavy hair. Her eyes were ringed with blue eyeshadow, and her lips were unpainted. She had also dressed casually in pale blue trousers, and a tight-ish black top. I guessed she was probably around a size fourteen, certainly not a big girl, but not as in shape as she could be, even at her age. Her breasts were probably around a C cup, but what really interested me was when she turned to lead me into the kitchen, her trousers were tightly stretched over her ass, and there was no visible panties, she may have been going commando. I mentally licked my lips.

 "My husband’s in china this week, " she commented over her shoulder as she entered the kitchen and leaned up against the breakfast bar.  "With his young blonde secretary I would imagine. " she continued darkly,  "But that doesn’t matter tonight does it. " she said as she ran a hand down my chest. This was obviously a lady that was wanting some cock, and wasn’t going to beat around the bush.  "I’ve never had an escort before, " she continued,  "I guess your job is to fuck me tonight yes? "

I decided to make sure she realized that I was as ready as she was, I took her hand and moved it down to my hardening cock,  "My job Tracey, " I said,  "Is to please you in anyway you want. " Her hand gripped my cock, and her eyes widened appreciatively.

 "Do you want a drink David? " she asked, licking her lips slightly,

 "Sure " I smiled back.

 "Good " she shot straight back, then reaching down, she undid the snap of her trousers and pulled them down, revealing her wispy haired pussy. I had been right she was wearing no panties.  "Why don’t you take a taste. " she sat on a stool, and spread her legs wide.

Some ladies that book me, because their husbands don’t pay enough attention, or who aren’t good enough in some way, are quite nervous at the thought of cheating on them. Tracey certainly wasn’t nervous, her pussy was already gleaming, and her lips looked puffy, she had obviously been playing with herself and getting nice and horny before I even arrived. Bending down onto one knee, I lifted her left leg, and placed it over my right shoulder, then taking her right leg, I held it so she was spread as wide as possible. Then taking a deep breath, I ran my tongue over her lips and up to her clit. The response was breathtaking, her lips opened before me, she had obviously brought herself to at least one orgasm before I had arrived if not more, and her clit poked out. I immediately blew gently on it making her whole body shiver, before taking her clit in my mouth and sucking greedily on it.

 "Oh suck it David, suck my clitty. " I did as I was asked, and continued sucking nice and hard on her erect clit, while occasionally nipping it with my teeth. Every time I did so she moaned. It turned me on as it always did to hear someone old enough to be my mum, moaning because I was eating her pussy out.

I took my free hand, the one that wasn’t holding her right leg, and started to rub at her pussy lips. It didn’t take a second to slide a couple of fingers deep inside her. She had obviously had children, the stretch marks, proved that, but her pussy was quite loose. I had no idea what size vibrator or dildo she’d had inside her, but it’d probably been big. Possibly bigger than me, but I’d always backed myself to more than make up for my lack of size with technique. She obviously liked having the fingers inside her as she started to grind down on them, so I made the most of her loose pussy, and slide another in, and another until all four fingers were penetrating her cunt, which I let my mouth and tongue take care of that clit.

She was steadying herself with her hands flat on the table as I continued to pleasure her orally. I could feel her whole body begin to shake as I flicked licked, sucked, and bit her clit, while constantly shafting her with all four fingers. It didn’t take long for it all to become too much, and with a low groan she started to cum. I quickly whipped my fingers out, and jammed my tongue into her pussy making sure I drank as much of her cum as I could get. Finally when her body relaxed I removed my mouth, and standing again, slowly licked the sweet salty love juice off my fingers.

 "Uhhhh " she managed to groan,  "That was incredible, why can’t all men be that good. "

I grinned,  "Because I’d be out of a job! " I joked.

 "You will never be out of a job David, " she said seriously,  "Now I think it’s time I showed you the bedroom. " She got down off the stool, not caring that she had leaked juice all over it, and ignoring the trousers on the floor, she took my hand and led me upstairs.

The bedroom was the standard affair, a little girly for my taste, but it did have a nice big double bed, with a bedside table on the side. On the table was a long thin vibrator, obviously still glinting with cum. She sat on the bed and gestured me to the other side of the room. I guessed what was coming…

 "You’ll do whatever it takes to please me? " she asked again.

 "Definitly " I replied.

She paused, then said,  "I’ve always been turned on by the thought of a young stud like you masturbating for me. Building himself to a climax then cumming all over my tits and face. It said on your website you are capable of multiple performances, why don’t you make your first a real performance. " This lady was expecting big things from me, but I wasn’t surprised, it was a common fantasy, especially among older ladies that had low sex-esteem.

I nodded, then asked,  "So you want a show? "

 "Oh yes " she replied. She repositioned herself on the bed, so her back was against the headboard, her legs spread wide so i could see her pussy. She quickly reached down and pulled the top over her head, revealing that along with no panties, she had no bra on. Her tits were definitely sagging, but still attractive, her nipples were small and pale, but I knew I’d still enjoy a taste.

I stood forward a little so I was half-way between the bed and the wall. Then slowly started to move my body. I do numerous strip shows as well as my evening assignments, and while I’m no great dancer, I can move my body. As I twisted, bucked and spun, Tracey started to finger herself, just playing with her clit at first, before moving to slide a couple of fingers inside. I quickly took hold of the hem of my tee, and quickly brought it up and over my head. She sighed softly, as my chest came into view. I continued to move making sure she got a good view of my chest and back, and occasionally bending over letting her see my ass pressing tightly against my jeans.

Turning back towards her I swayed my hips some more, before undoing the top button of my jeans. I had selected a pair of jeans this evening that had a button fly. After plenty of feedback from women I had realized that button flies were much preferred by the ladies. Tracey obviously shared this love as she paused in her pussy playing to rub one of her tits gently before sliding her hand back down to diddling her clit again. I started walking towards the bed, undoing a button every step. It took three steps to reach the bed, which meant that there was only one button left, which in turn this mean that my bulging boxers were clearly on show. Standing at the edge of the bed I undid the final snap, and pushed my jeans to my ankles, slipping off my shoes at the same time. I started to rub my cock over my boxers, and Tracey went wild.

Her head lolled back against the wall, and her fingers went at light speed on her pussy. I decided to knock it up a gear and stepped onto the bed. The movement of the bed, concentrated her mind again, and she looked at me with glazed eyes. I couldn’t stand straight on the bed, because the ceiling was too low, but I crawled towards her, then knelt up around a foot or so away from her. I started rubbing at my cock again over my boxers, purposefully deepening my breathing, and being more vocal every time I breathed in and out. This sex starved older lady’s eyes were locked on my cock. I turned on the bed, and she groaned in disappointment. However I was planning to remove that disappointment quickly. I took hold of the hem of my boxers, and slid it over my ass slowly letting Tracey see my tight ass. She groaned again, this time in pleasure not disappointment. Keeping my eyes facing front, I started to rotate my hips letting my ass shake and move, it wasn’t long until I felt a hand reach out, a slightly damp hand at that, the hand squeezed and tightened on my ass, rubbing and pressing at it frantically. I encouraged her more pushing my ass back into her hand and letting her play. It was strictly against the rules of me performing for her, but she was enjoying herself, and I didn’t want to spoil her fun.

After a few moments of my ass being rubbed and played with, I pulled away from her again, slipping my boxers back on over my ass I stepped off the bed, turning back to face her. Her face was bright red, and she’d obviously enjoyed the time with my ass immensly. Again I began to move and shake, caressing my own chest and cock. Tracey reached over to the bedside table, and retrieved the long vibrator. Switching it on she slowly inserted it deep inside her, moaning softly as she did so.

I felt it was time she saw a real toy. So hooking my fingers in my waistband once more, I dropped my boxers in one fluid motion, revealing my rock hard seven-inch cock to this old sexpot. I turned to give her a view in profile, then back to front facing, then profile on the other side, as Tracey started to drive the vibrator deeper into her soaked pussy. I took my shaved balls in my hand and massaged them slowly, making my rod dance and jerk, before taking my free hand and sliding my finger tips up and down my cock. Putting one foot on the bed, I started to rub it with earnest. Stroking it back and forth, gazing at her as I did so.

Her breathing was ragged and her vibrator rhythm was off by this point but she still managed to gasp out,  "Come closer stud. " I didn’t tease her, but mounted the bed once more and knelt between her legs, pointing my cock at her face as I slowly increased my speed. I took my other hand off my balls, and reached down, pulling the vibrator out for a moment, then rubbing her pussy gently, this had the happy effective of a nice sticky mess of cum all over my fingers. I quickly swapped hands and started pumping my cock with my lubricated hand. I began to buck and rotate my hips as I did so, building myself into a frenzy. Her eyes and mouth were wide as my hand blurred over my cock.

I could feel the fire building, and knew that the sooner I came, the sooner I would be ready for more with this horny old lady, so instead of restricting it as usual, I let it build, before without any warning, I let out a shout, and fired my load straight into her face. The first shot slapped over her nose and in her mouth. She immediately extended her tongue and I managed to aim the second shot right onto it. The third was directed onto her eyes and forehead, then the fourth and fifth, minor pulses were sent onto those saggy tits.

She quickly licked her lips, and started to rub her tits, rubbing in my cum,  "It’s good for the complexion you know! " she stated primly as I looked on. Once she was satisfied that it was all rubbed in, and she’d managed to taste every bit she could. She took hold of my rapidly deflating cock, and slid it straight into her mouth.

I go a lot smaller when I deflate, than when I’m hard, in fact my length drops a couple of inches, so she managed quite easily to fit the whole of my soft cock in her mouth. I thought she was just going to clean it off at first, but she had bigger things in mind.

Slowly she massaged my cock with her mouth and tongue. She reached around to grab my ass again and she began rubbing and squeezing it. I reached down and rubbed over her tit, making her nipple stick out. She moaned round my cock and began to suck me harder. I took her nipple in finger and thumb and started to tweak and tease it, encouraging her in her efforts. I felt my cock begin to harden again.

We continued this for a good half hour, her mouth slowly getting filled by my hardening cock, and her nipple constantly being twisted and pulled. The moans grew louder, and more muffled the more cock she had in her mouth.

I groaned loudly, this lady knew how to suck cock. I was finally ready to go again, but she just didn’t stop. She started bobbing her head up and down on my fully erect 7incher. Moving her second hand to my ass to enable her to force as much into her mouth as possible. I left her, by now, bright red nipple, and move my hands to her head, aiding her sucking efforts. Eventually she her mouth off my cock, her chest heaving, her breath panting. When she caught her breath she leant over to the table again, and taking a condom out, she opened it and slid it over my cock, saying,  "My husband, has only ever fucked me missionary. I want you to fuck me in the most imaginative and dirty ways possible in his own bed. I want to feel this big sexy young cock deep inside me in every way. "

That was all the encouragement I needed, I took her and roughly turned her, pushing her into the doggy position. She grasped the headboard, instinctively realising that she would need a stable footing for what was to come. I slapped her ass once, twice, three times, each time illiciting a deep guttural moan from Tracey. Then I spread her ass with my hands and aimed my cock at her entrance.  "Uhhh fuck me, fuck me stud. " Tracey groaned. Holding her ass spread wide, and slammed my hips forward ramming my cock deep in her cunt.  "FUCK! " she shouted as I penetrated ball deep inside her. Then slowly I withdrew, maximizing the time My cock was moving out of her. Then just as I slid out of her pussy, I rammed back in as hard as I could,  "FUCK! " she cried again. Again I slowly drew out and rammed back in, and again the  "FUCK! " cry burst from her lips. Five times I did that building her anticipation for the finale. On the fifth time as I drove back in I spanked her ass again, harder this time, although this time instead of drawing out slowly, I moved out quicker, and slammed in again. Starting to piston my cock in and out of her loose old pussy. This time instead of verbalizing she was merely grunted as I sawed in and out of her pussy. Building my speed and power as I fucked her I reached round and grabbed one of her tits, squeezing it hard. Her grunts ran into each other as my speed built, so she was sounding like a cave woman grunting by the end of it. The grunts increased in volume as I fucked her, until eventually the grunts turned to a moan, and into a barely heard,  "Fucccccckkkkkkk I’mmmm cummmmiiinnnggg! " I immediately pulled out, and jammed my face in her pussy, diddling her clit with my tongue as I tried to suck as much of her nectar as I could. When she was done, i removed my face, and let her sit up. Her face was even more flushed, her makeup had run, and she looked like she had been ravished.

I took her tits in my hand and bent to suck on those nipples, her grunts returned as soon as my tongue hit her nipple. After a brief nibble, I removed my mouth, and sat on the bed, commanding her,  "I want you to ride me! "

 "Ohh yes! " she moaned, spreading her legs and poising over me. I lined up my cock with her pussy, and she slowly settled down on it, sliding her soaked loose pussy as far down as it would go on my cock. She started to move up again but I stopped her by holding her hips down,  "Wait baby, I want to enjoy the sensation of being fully in you, before you ride my big cock. " I realized that while she had been in charge at the start, my strip and masturbate had put me firmly in the driving seat.

 "Uhhh yes baby, I love the feel of this hot young cock inside me. "

Eventually after moving my hips and making sure I was comfortable, I said,  "Now ride me baby, work my cock, grind your pussy on my meat. " I let go of her hips, and she immediately started bouncing up and down on my cock, moving her legs and hips so her pussy slid up and down on my cock. I reached round and grabbed her ass, and squeezed and kneaded it like she’d done to me. Her breathing went ragged again and her rhythm quickly was lost, but she kept up her speed, her ass jiggling as it fucked up and down my rod.

 "Spank me stud. " she managed to gasp out, and I complied happily, every time her pussy was fully impaled on my cock I spanked her nice and hard on her ass. She moaned again and I felt her pussy explode round me once more. I took hold of her hips and made sure that she didn’t slow down, just because she’d cum. Credit to her however she continued bouncing, her tits bouncing as wildly as her ass was. It wasn’t long however before her breathing deepened again, the moans grew louder and once more her pussy exploded all over my cock. That was the last of her energy though, and she collapsed on my body, letting my cock slip from its prison. I realized that although she’d booked me for the night, she wouldn’t be able to go all night long, in fact she probably only had enough energy for one more fuck, and I’d have to do all the work. I looked at the clock, it was still only just 11.

 "I’ve never cum so much " she moaned as she slid off my body.

 "Well how about I finish you off then. " I said a gleam in my eye.

 "How, I’m not sure how much energy I have. " she commentated.

 "Have you ever had a cock inside your ass? " I asked

Her face told the whole story, fear and desire were mixed, she paused a moment, obviously thinking,  "You’ll…you’ll be gentle? "

I knew I had won, I’d be fucking this old ass.  "Of course, anytime you want me to stop, just shout the word, ’Darwin’ " Darwin was the safety word i always used.

She took a deep breath,  "OK, fuck me in the ass. "

I kissed her, the first time I had that evening, then told her,  "Get back in the doggy position, and hold on tight. " I quickly threw away the condom and replaced it with a new one.

I spread her ass again with my hands, revealing her pussy and tight little pucker. I started my tongue inside her pussy, licking her, and getting as much cum on my tongue as I could, then I licked up from her pussy to her ass hole, and teased it with lots of little licks, then I repeated the process. Tracey was moaning constantly, the thought of her ass being licked by a young stud while her husband was away was proving too much for her.

I continued to lick her ass out, using my tongue to test how tight her opening was. When I deemed that she was ready, I slid a finger deep inside her pussy, coating it with cum, then started to finger her ass. It didn’t take long for her ass to loosen, and soon I was knuckle deep in her ass hole. Her groans grew louder and more guttural, as I forced my finger deeper until it was all the way inside. I worked it round and round, widening her hole ready for my cock.  "Do you like my finger in your ass Tracey? " I asked her.

 "Urrrghhh David, it’s amazing, it feels so good, a little painful, but so, so good. "

 "Then just think how good it will feel in a moment when my cock slips in! " I murmured.

She didn’t reply she just groaned loudly.

After a few more minutes of ass play I thought she was close to being ready. I slid my cock inside her waiting pussy, and pumped it a few times to lubricate myself. Her pussy was a cum producing factory, she’d been soaked when I arrived this evening and she was still soaked now hours later. I positioned my head at the entrance to her ass, and slowly and carefully pressed it up her crack. She moaned, it obviously hurt, but I was relentless, I pushed further, gently trying to get inside that ass. Suddenly her butt muscles relaxed and my head popped in, and so did a couple of inches of cock. She screamed, ending it with a,  "Oh fuck, oh fuck, oh fuck, that’s good. " i took that as a sign to keep going, so started working back and forth in her ass, slowly opening her wide, and allowing more and more of my cock inside her. Eventually my full seven inches were deep in her ass. She wasn’t even groaning anymore, this old slut was just trying to get enough breath in her body. I started to move my hips back and forth, sawing in and out of her ass, first with little movements, but soon my whole length was sliding out, then all the way back into her ass hole. I sped up, and spanked her ass again for good measure, there was no response, she was so keyed into the pleasure of the moment she couldn’t bring herself to talk. I sped up again, soon I was pounding her ass, finally her silence broke and she started moaning, almost mewing like a cat as I fucked her ass. I felt my orgasm building and knew it was close, so I reached round and started to finger her pussy and clit as I fucked her ass. This broke her resistance, and soon she was screaming and shouting as a powerful orgasm rippled through her system, I kept it up until suddenly she collapsed on the bed, and her ass tightened momentarily, before relaxing. I slid out. She had obviously fallen unconscious. I slipped off the soiled condom, and quickly wanked myself to orgasm, cumming all over her ass and back.

She didn’t wake until 6 the next morning, when she did she stared at me, her hair wild, her eyes glazed.  "It wasn’t a dream? " she questioned wearily,

I smiled at her,  "Nope I fucked you in your pussy in your mouth and up your ass, and you’ve been covered in my cum. "

She turned to a photo, presumably of her husband,  "Take that Arsewipe. "

I dressed and left my card with her, and left, a little early maybe, but she was in no mood to stop me, a week later I got this email.

Dear David,

My ass still hurts! I enjoyed our evening immensely, and only wish I could have been conscious for more of it. My husband came home, to find a citation for divorce. I’m expected to get a sizable portion of money and the house from the settlement, so expect to have your services called upon on a regular basis. Tracey. x

I suggested to her that she may wish to go for evening assignments in future, and she agreed. I had another three of four bookings from her before she decided against making more, I’ve no idea why, I do know that fucking someone that old was a unique thrill for me.

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