Milf Escort Did I Dare

My short story tells the story of a time I visited a local escort, I have changed names and certain details so as to maintain privacy. I hope you enjoy it.

My days were blurring into one another, monotonous into monotonous. I was exhausted and drained; I didn't want to do this daily, I didn't like my job. It wasn't difficult, but it was the same frustrations day after day; dealing with the same idiots was very draining. I am meant to go into the office at least two days a week, but working in IT and being a middle manager warranted certain rewards, one being that I only went into the office less than once during a full moon. I know what you are thinking, "change your job" I would, but I'm paid well and have a lot of flexibility, allowing me to live my life how I need to.

I often tried to break up my days by watching a film on one of the many apps I paid for, as well as watching a little porn. It was whilst watching porn that I stumbled on a website promoting local Escorts, 'Adult Work'. At first, I was fascinated and intrigued by what constitutes an Escort in today's world. Are there differing standards? What generally does a typical escort look like? And finally, how much does it cost?

I was surprised at how many Escorts were within 5 miles of where I lived and even more surprised if I widened the search to 10 Miles. The search function was brilliant; you could narrow the search to every like or every want! Blonde, brunette, shaved, not shaved, breast size, absolutely everything. I was like a kid in a sweet shop, although it did take me a little time to get used to the search function to return a good number of escorts in the search. You could be 'picky' but not highly picky as trying to find the perfect woman was like trying to create your own in the film 'Weird Science' (yes, I'm that old). It would be great if I could find a 'Kelly Lebrock' though. The search wouldn't return anything if you clicked too many different things. Additionally, I had to google many of the likes (the services provided) as I had no clue what most of the acronyms meant. To this day, there are still a couple that baffles me; I mean, come on, what is Bukkake, and what are 'A-Levels'?

At first, and for quite some time, I acted truly like I was window shopping. The more I landed on the website each day, the more intense my desire to enact an actual escort meeting. Over time, I'd built up a couple of excellent saved searches, and on clicking on them each day and depending on availability, I got used to the exact escorts being returned. After quite some months, I had a generous 'Hot List' which, if scrutinised, was made up of aged women or, referring to them in the website's terminology, a 'MILF'. I was starting to get an itch that I needed to scratch!

I stumbled upon one profile; she had her own website and many blogs about many differing sexually-orientated subjects. She was a MILF, and from her pictures, very alluring, I was drawn in. For a few weeks, I debated whether I should or not, did I dare? Then, one morning, I decided to send her an e-mail. It went along the lines of:

"Hi Kerry, how's things?

I was reading your blog about 'How to please a Woman' and the 3 hour session you provide on the same. I am very much interested in the session but was hoping for a bit more detail so as to know what to expect and what in full will happen during the session. I suspect like every man I have a lot to learn and just don't know it yet and you explain that during the session there is a 'practical' experience. How 'practical' is this and is it two way? The reason I ask is that I can imagine that as I am exploring your body and your most sensitive parts it would lead to a great deal of 'excitement' on my part which will lead to a great deal of urges that will take a lot of self control. How far would/should I take those urges, what would you also expect?"

You can see my naivety in my email. After reading it back, I regretted the wording because she would have known how new to all of this I was. I should have kept it short and sweet, but I had to be me and ask lots of questions and specifics. Doh!

I did get a reply though a few days later:

"Hi James

Thank you for your message it is good to hear from you and it would be lovely to spend some time together I think the best thing you could do is give me a call and we can have a conversation around this as it's a lot better than emailing

You will get me on the phone between 7 am and 9 am on my working days

I very much look forward to hearing from you and it would be lovely to meet you at some point in the not too distant future

K x"

I instantly had a cold sweat and felt scared and worried; she wanted me to call her, but I didn't think I was brave enough to do that. I left it as was for a few days and then, from somewhere, plucked up the courage to call her. My mouth was dry, and when she picked up, I tried to say "hello", but all that came out was a squeak. I coughed, cleared my throat and tried to act bravely; I'm sure she could see through me. Our call lasted all of 5 minutes, and by the end, I'd booked a two-hour session that was now in the diary for four weeks.

Instantly I was filled with regret, and 100% I was shitting my pants. As the day grew closer, I convinced myself there was no way I could go through with this, and sure enough, I bottled it. I sent the escort an e-mail letting her know that I needed to cancel the appointment, that I was sorry and that I knew I would probably be excluded from ever being able to secure a future appointment with her. She was grateful I'd cancelled in good time, but her reply was icy.

Well, that was a success, not!

For the next 12 months, I continued window shopping, finessing my searches, administrating my 'Hotlist' and dreaming of having the bravery to follow through on an appointment. I knew I would be wasting an escort's time, which wouldn't be looked upon favourably, but I did e-mail a few. I'd got to the point where I thought, "I can do this", only to receive terse, uninterested replies which put me off totally. I then again stumbled upon a profile, a 55-year-old MILF, with dark hair, small breasts and quite petite, not really the type I would typically go for. There was just something about her; perhaps it was the fact that she had hundreds of free pictures on her profile and many of those allowed the punter to see her face (which many of the other Escort profiles didn't do). I often wondered why an escort wouldn't show her face in the pictures. I suspected it was due to many reasons, but I suspect the main one was privacy, not being recognised by family and friends. From somewhere, I gained the courage to email her; this time, I kept it very simple and straight to the point:

"Hey, how's things? Are you available tomorrow (Tuesday 30th April) in the morning? 9:30/10 am. 1 hour appointment. James"

Sure enough, I received a quick reply:

"Hi James, Yes I am, shall I book you in? Paula xx"

We corresponded some more, and by the end of Monday morning, I had an appointment for the next day. Perhaps the short wait for the appointment gave me the confidence to follow through this time.

Tuesday arrived quickly; to say I was shitting my pants was an understatement; I was physically shaking during the drive to the address I had been given.

This is not the story, meeting, or experience I want to tell you, so I will skip many details and give you the bullet points. Paula was a nut case; there, I said it, a completely crazy nut job. It was immediately noticeable, but with the things she said and did, the vibes I got, she was a nutcase. Granted, she was dressed in all the gear: lacey underwear, stockings, suspender belt, the whole deal; she looked the part.

I was led upstairs, paid my fee and got down to business. Let's say I was able to please her at least once orally before she reciprocated, and then I slipped on protection to take her doggy style. She kept saying, "I'm mad me", and she was unwilling to remove her stockings. I didn't want to hang around very long after finishing! I didn't want to take the risk of how crazy she was. The suspicious side of me often wondered why escorts do what they do (I made a mental note that if I ever did this again, I would ask). Is there a negative side where men perhaps get blackmailed in some way? I suppose this shows my naivety.

Reflecting on my very first experience with an escort, I regretted everything. I wondered why I'd chosen her; even months later, I couldn't work it out. She was quickly removed from my Hotlist, and I tried to forget the encounter soon.

I know I had a bad first encounter. I suspected it would be some time before I plucked up the courage to do it again, but this didn't stop my window shopping, which broke up my day. Months later, after tweaking my searches several times, a new profile started being returned, one I'd not seen before; it was always exciting to see a new profile pop up. 'SimplyCharlotte' (profile name changed for this story) was different from the other profiles; there was just something in its simplicity that made Charlotte very appealing. With only six photos, no head or face shots, and no private photo, I was intrigued, especially as she was within my radius of 10 miles. For weeks, I kept returning to her profile, hoping for more photos or different content, but whilst some of her literature changed slightly, the images didn't. I could see she was voluptuous but not fat, with incredible cleavage (I wanted to see the rest that had been perfectly hidden), slender legs and, from the small glimpses in the photo, smooth skin with a button nose. I needed to see more, but dare I request an appointment? Would she turn crazy? What if something terrible happened?

I read through her profile multiple times, appealing aspects that jumped out to me:

How would you describe your body type? Curvy

How tall are you? 5'5"

What is your dress size? 14

What is your bra cup-size? DD

How would you describe the size of your breasts? Medium

Are your breasts natural or enhanced? Natural

How is your pubic hair fashioned? Shaved Mostly

Then there were Charlotte's likes, or as per the website, what Charlotte enjoys:

Foot Worship, French Kissing, French Kissing (discretion), Hand Relief, Massage, Oral, Oral without (at discretion), Oral without Protection, Penetration (Protected), Receiving Oral, Spanking (giving), Spanking (receiving)

It was simple, straight to the point, and very clear, so there would be no ambiguity if I visited Charlotte about what we can and can't do; I started thinking I should at least e-mail her. I plucked up the courage the next day, intentionally trying to keep it short and sweet as I had seen on many profiles the women did not like too much correspondence; the e-mail I sent went along the lines of:

"Hi Charlotte, how's things?

It is the first time your profile has popped up in my searches, and I wanted to say that it is good and that you sound wonderful.

I know you are listed as close by, but would you be willing to share the postcode so I can judge the distance?

Thanks in advance, I hope you have a great day.

James"

We exchanged correspondence for the next few days; I felt Charlotte was accommodating and humouring me in her very friendly replies. I regularly continued 'window shopping' for the next few weeks, returning to Charlotte's profile; I can only think I did this to pluck up the courage to arrange a meeting. After another couple of weeks, I eventually decided I was going to contact her again, and I felt I was ready, so I reread her profile and sent her precisely what she had asked for:

Hey Charlotte, I hope you are well.

I wanted to check on your availability today, preferably before 4 p.m. I am 48, and my name is James. I think it's a 30-minute drive to you.

I hope you have a great day, even if you have no availability. It looks like it's going to stay dry out there, making for great walking weather.

Also, you have added fantastic new photos; it would be rude to tell you which ones are my favourites.

Have a good one.

James

At 48, I wasn't too beat up, alright, I was no George Clooney, but I was no 'Sloth' from the Goonies film either; I'd done alright through my life with the ladies. Yes, I was overweight, but I hadn't played football for a while now due to both broken ribs (football injury) and a slipped disc. I wasn't a huge pie muncher, though! Why the need to visit an escort? I asked myself that question several times but never gave a straightforward answer; I suppose it excited me. I don't think it's me you want to know about, so I'll continue my story....

Charlotte had confirmed that she could meet with me the same day, and after a couple more emails, I had her location and instructions for what I needed to do when I arrived. It was now that the nerves kicked in, as well as the excitement, doubts, self-questioning, and wondering what Charlotte would be like in real life. Three showers later throughout the morning, a change of wardrobe twice, and I drove the 30 minutes to Charlotte's location.

I was always early for everyday things like going out or parties. It was one of my bad traits, but I saw it as good. So, I pinged Charlotte. I got no response, and the panic set in. I decided to call her on the number she'd added to her e-mail.

"Hey, is that Charlotte"? I said with my most confident voice, "It's James. I'm so sorry, but I'm slightly early".

A soft voice said, "Awww, that's okay, James. It's not a problem. Drive your car onto my driveway, park up, and come to the door. I'm so glad you are here".

I instantly felt a little at ease. She sounded nice, and I wondered who would match the voice. My excitement grew even more. I quickly drove a few metres and parked up on Charlotte's driveway. Getting out of the car, I locked it and walked the very short distance to her door. I knocked quietly, and a voice from inside said, "Hey, James, come on in".

In our communications confirming the appointment, Charlotte asked if there was anything specific that I wanted her to wear. Whilst a lady in sexy lingerie, lacy material, thigh-highs, suspender belts, etc, looked good, I'd asked if she could dress casually. Specifically, I'd asked her to imagine she was having a lazy day at home lying on the sofa, reading a book or watching a film. I know you are asking, "Are you crazy, James? Why would you not opt for the sexy lacy clothing"? Honestly, I just thought we'd both be comfortable, relaxed and with no pressure; I can't explain it better than that. Perhaps if there were a repeat visit, I would ask Charlotte to go full lace, but let's see.

Walking through the door, I entered a dimly lit kitchen. Charlotte appeared from behind the door with a huge smile, and before I could look her up and down, we were in full embrace, a nice welcoming hug. We parted, and Charlotte said something warm and encouraging. I honestly can't remember as I wasn't entirely with it, as I tried to take in as much of Charlotte as possible visibly. What I saw brought a smile to my face. My thoughts rapidly from the day of what I wanted or was going to do with Charlotte rushed through my mind; I was going to orally please her to a climax as many times as she would let me; I would penetrate her with my fingers first before positioning us into a 69 before fucking her from behind. A sweet, kind voice brought me back to the now, "How about I show you around my house? I'm very proud of my work in progress". Charlotte took my hand and led me from the kitchen into a large living room.

At this point, I was able to take in the incredible view in front of me; I was instantly drawn to her beckoning cleavage wrapped tightly in a polka dot dress. I tried my hardest not to fixate too much on her beautiful breasts to notice how pretty she was. Yes, she was a MILF, and, as her profile suggested, in her forties, but I could already see her skin was smooth, silky almost; I was dying to unwrap her. I got a hint of a floral perfume, which was intoxicating, and I could smell also a floral shampoo wafting from her hair. Charlotte had little to no makeup on, perhaps a little lipstick at most, which was perfect. I could see now that her wavy dark blonde with tints hair fell to just past her shoulders and, if it fell wrong, blocked my view of that beautiful cleavage.

As Charlotte led me through each room of her house, I could see there wasn't much furniture or decoration. She explained that she had recently purchased the house and was renovating it while she lived with her parents. If I hadn't been so eager to unwrap the present that stood before me, I could have easily sat down with Charlotte and chatted for hours; it was clear she was that type of lady, easy to talk to and get on with. I continued to follow her from room to room, watching her curves sway with each step she took, the figure-hugging dress accentuating her curves, causing my eagerness to increase to grab hold of her and make her mine.

Eventually, Charlotte led me to the bedroom where all the magic happened; that sounded better than Charlotte leading me to the bedroom where she performed her escorting role. My naivety is raising its ugly head; I fumbled both vocally and physically in trying to give her the fee for my one-hour session. She again put me at ease, taking the money from me and offering a clean towel, asking if I wanted to shower first. I explained in all my nervousness and excitement that I had showered three times and only driven for 30 minutes, so I was ultra clean, which she said was fine. I did think, though, what if I'd accepted? Could I have persuaded her to join me so I could get her all soapy and explore her body? Perhaps one for next time, or even a bath together, sounded terrific.

I stripped, trying not to look too eager. Everything came off, and Charlotte helped place the clothes neatly on a chair. I'm sure I lost a few seconds because I do not recall at what point she had slipped the polka-dot dress off; I felt a little cheated; I wanted to see the action of it coming off. Whilst I was completely naked, Charlotte stood there; in matching black bra and knickers, there was nothing fancy about them and exactly what I'd asked for.

Throughout all this, Charlotte talked to me reassuringly; she asked questions, not private ones. I could sense she didn't want to delve into my circumstances. I did wonder about her, though: who was this person standing in front of me, a stranger I hoped I was seconds away from being fully naked with? "How about you lay on the bed, and we can start with a nice massage"?

Charlotte brought me back from my thoughts. Before that, I wanted to break the ice first, even though, to Charlotte, I suspected there was no ice to break, "I'd love to kiss you first if that's ok"? I felt slightly foolish for a split second, asking if we could kiss; what were we, twelve? She instantly threw her arms around my neck as we merged mouths into a full embrace, kissing for what seemed like an eternity, our juices mixing and tongues dancing, her lips soft and moist. She broke the kiss, "Hmmm, that was nice; you are a great kisser, James; now lay down", she said, laughing. I did as I was told but wondered if she had said that to all the boys.

Laid on my front, Charlotte started massaging my upper body. I honestly can't remember what we talked about; it felt wonderful to have her hands exploring my body. When she got lower, Charlotte did pass comment on my legs; having played football all my life, they were big and muscular; I think from her remarks, she liked them. I don't know how long I was under Charlotte's spell, but eventually, she said, "My turn".