I’ve been having an ongoing affair for a couple of years now with a married lady of a similar age to myself, called Charlotte.

We met through work and had an instant attraction to each other. All the clichés about chemistry were true and remain so to this day. Within a month of our first meeting, which was through work, we were arranging to meet in hotel rooms for afternoons of the filthiest sex I have ever experienced. For reasons I still can’t quite fathom, we’ve always been able to be completely open and honest with each and our pillow talk soon revolved around sharing our most intimate sexual fantasies.

I asked Charlotte whether she’d ever had any same-sex experiences, any group sex and the other usual perverted events that most likely swim around every man’s mind. I was amazed that this beautiful, sexual woman who lay naked next to me had actually led a very conservative past. She hadn’t experienced anything anyone would consider unusual, she had never watched pornography, had never used a sex toy and her sex life at home was entirely vanilla! I was obviously very keen to enlighten Charlotte to the wonders of all of the above and we spent the next few months meeting as often as possible and would spend our recovery time watching porn on my iPad, finding out all the things that would turn Charlotte on.

If you were in the lucky position that I was in, you would not recognise the Charlotte of those days to the Charlotte of the present day. She may look the same from the outside, but in the past two years we have used every kind of sex toy available, we have explored our dominant and submissive sides and have realised we both have a previously unknown desire for urination during sex. Perhaps the most incredible thing to have happened over this time, is how Charlotte’s dominant side has become more prevalent and my own submissive side has done the same. The whole dynamic of our sexual relationship has changed and the events that I’m going to concentrate on will hopefully reflect that.

I first noticed a noticeable change in Charlotte, when we spent our first night together in Wales, last year. We had spent many afternoons fucking in hotel rooms but this was the first time I was going to wake up with Charlotte. During our previous liaisons, I had introduced sex toys into our play but always me using them on Charlotte or me watching her use them on herself. On this occasion, I had bought a new sex toy, which was a relatively small latex dildo that sat on top of my own cock, kept in place by a tight hoop that my erect cock would push through. I was trying to introduce Charlotte to anal play and had previously used a couple of fingers inside her tight hole when I was eating her pussy. She was very open to the idea of anything and I was confident this would be the night when I would get to fuck her arse.

I’ll always remember the image of Charlotte laying naked on the bed with a couple of pillows under her waist. I eased my cock into her soaking wet pussy and using some lube, pushed the small dildo in her arsehole. The latex and lube opened Charlotte’s arsehole with ease and I was soon penetrating both her holes as I fucked her hard from behind. She screamed in a mixture of pleasure and pain, which soon gave way to an incredible orgasm for both of us and I shot my hot load straight into her pussy. As I pulled out of her, her arsehole remained open and I gave her tight bud a kiss and explored her hole with my tongue. We had definitely crossed a line where anything was possible!

As we lay on the bed, Charlotte began asking me about my own sexual history, something which she had not done before. I was completely honest with her and told her that I have had some gay experiences but had only ever really sucked cock. I had never been fucked by a man but had used a dildo on myself. Charlotte was stroking my cock back to health as we spoke and I could tell she liked hearing my stories in as much detail as possible.

“So you’ve had a cock in your mouth?” she asked.

“Yes. Quite a few times,” I told her.

“Do you like the taste of cum?” she asked.

I had to admit that I did and I told her so.

Charlotte had begun stroking her pussy as we spoke and I assumed she was going to bring herself to another orgasm but this was not the case. Charlotte had pushed two fingers inside of herself and with my cum visibly dripping from her fingers, she brought them up to my mouth.

“Show me,” she said.

I looked at the cum covered fingers in front of me and began to lick the juices from her, eventually taking the fingers in my mouth and sucking them. Charlotte sat up so she was kneeling on the bed. She took a larger dildo from the bedside table where we had previously put them and pushed it inside her sopping wet cunt. She thrust in and out a couple of times before bringing the dildo up to my mouth and without warning, forcing it down my throat. I was gagging on the length of it but took as much as I could in and sucked the musky mix of juices from it.

Charlotte continued to fuck my mouth with the dildo and used her free hand to wank my cock, which was now as stiff as it had ever been. She took the dildo out of my aching mouth and leaning over me, she began to suck my cock. She reached her other hand under my balls and began circling my own arsehole, something she had never done before. She pushed a finger inside me but with her long nails, it was rather uncomfortable.

“Please use some lube,” I told her.

Charlotte moved down to the bottom of the bed so she was now kneeling on the floor. She pushed my legs up and began to lap her tongue over my arsehole. I have been very lucky to have had some incredible sexual experiences but having a tongue in my arsehole was the most amazing feeling I have ever been on the receiving end of. I can only describe it as having lots of small orgasms every time her tongue circled my arse and when Charlotte attempted to push her finger into my hole once more, there was no discomfort whatsoever!

As I lay back on the bed in complete ecstasy I could feel Charlotte push another finger into my arse. My groans would have told her easily enough just what this was doing to me and she began fingering me roughly.

“Oh God, you really like that, don’t you?” she asked.

“Fuck, it feels amazing!” I told her.

Charlotte picked up the small latex dildo that had been in her own arsehole only an hour previously and pushed it straight into my loosening arse. I had fucked myself with dildos before so I was used to the pleasure it gave me, but looking down and seeing a beautiful naked woman with her tits swaying as she fucks you is the most erotic thing I have ever known.

Charlotte wanked my cock as she fucked me with the small dildo and would occasionally suck my cock for good measure. Charlotte loved to swallow my cum, so I was sure she would want to do the same again and I knew she wouldn’t have long to wait.

“I’m going to cum!” I shouted.

Sure enough, with the dildo still pushed inside my arsehole, Charlotte took my cock into her mouth and sucked every ounce of cum from inside of me. She then crawled up the bed and kissed me deeply. She hadn’t swallowed any of the cum and as we kissed, my own hot juices flooded my mouth and our tongues shared and explored the wonderful cocktail.

“That was incredible,” Charlotte said.

“Yes, it was,” I enthusiastically agreed.

“Would you do that again?” she asked.

“Of course I would. We’ll have to make sure we buy a strap-on next time!” I told her.

“A what?” Charlotte asked.

I laughed. I couldn’t believe that even after what had just happened, she was still so naïve that she didn’t know any of these things existed. I grabbed my iPad and showed her images of strap-on dildos and found some pegging videos online, which we both watched with great interest.

“Oh, my god! Would you let me do that to you?” Charlotte asked.

“Of course I would,” I told her.

Things were never going to be the same again after that.

That same night, Charlotte had me on all fours as she used the larger dildo on me. I remember driving back home the following morning, my arsehole sore, well and truly fucked, thinking how it was supposed to be the first time I got to fuck her arse and not the other way around.

Unfortunately, our nights spent together are few and far between but our afternoon sex sessions now always involved her fucking me with the strap-on dildo that I had purchased for her. I always had to eat my cum from her or lick it off her. Sometimes it was from her pussy, sometimes from her tits or face and finally when I got to fuck her arse, I would eat my semen from her tight puckered hole. Occasionally she would swallow when the passion got too much and she forgot herself but more often than not, as soon as I had cum inside her or over her, she would simply fall back on the bed.

“Clean me up,”she would order.

And I was always very willing.

It was a few months later when we spent the night together again, this time on a rare visit for her down South, in Colchester.

We were meeting on the Wednesday but we met for lunch on the Monday before. After lunch, we were walking back to our cars and it was pouring with rain.

“Get in my car.

I’ve got something for you," she told me.

I sat in the front passenger seat and Charlotte got in the driving seat. The rain hammered down on the car.

Charlotte reached across and got a carrier bag from the back seat and handed it to me. I looked inside but saw women’s underwear. I clearly looked confused.

“It’s for you," she told me.

“What do you mean. For me?” I asked.

“On Wednesday, I want you to get to the hotel first and be wearing that when I get there,” she replied calmly.

I pulled out a pair of black lacy knickers and still looked confused.

“There’s matching knickers and a bra, which should both fit you and there’s also some black hold up stockings,” she told me. “I’m going to text you when I’m parking and I want you to be wearing that when I enter the room,” she said.

I could feel my cock twitching at the prospect of what might happen and as Charlotte’s hand found its way to my crotch, I could feel it harden.

“It feels as though you’re okay with this? You did say you would do anything?” she asked.

“Of course I will,” I replied.

“Show me how much you like the idea," Charlotte demanded.

I looked around the car park. Thankfully it was raining so hard nobody would have been able to see in the car. I reached down and undid my flies and pulled my noticeable hard cock from my trousers. Charlotte began stroking me, groaning as she did. She leaned across my lap and took my cock in her mouth.

Lifting her head up, she spoke. “Wank into my mouth,” she told me.

I held her head down with one hand and masturbated my cock with the other. It is no word of a lie when I say that I lasted literally seconds before I shot my load into Charlotte’s mouth. My cock pulsated with each spasm and I thought I was never going to empty. Charlotte continued to groan as she took it all in her mouth. As she sat up my cum leaked from her mouth and ran down her chin. I knew by now what she liked and I licked the mess from her face and Charlotte rewarded me by forcing her tongue into my mouth and engulfing me once again with my own hot semen.

On the Wednesday, I sat in the hotel room. I was already fully erect, waiting for the message from Charlotte. At 2.30 pm, my phone illuminated. She was outside. I was already naked but for a gown, which I quickly threw off and put the black bra, knickers and stockings on. As ordered, I lay on the bed as the hotel door opened. Charlotte walked in, clothed in her typical working outfit of a blouse and a knee length sensible skirt. She held her overnight bag in her hand and looked stressed. She looked at me lying on the bed.

“I’ve got to go the bathroom. You stay there,” she said.

I was disappointed with her reaction and felt a bit stupid laying there dressed in women’s underwear. I was in half a mind to take it off.

Within a minute the bathroom door opened and Charlotte came back into the room, still dressed as before but now with a noticeable bulge underneath her skirt. She came over to the bed.

“You look amazing,” she told me.

She ran her hands over my body and my mood perked up!

Charlotte grabbed roughly at my bra as though she was squeezing my imaginary tits. Her hand mauled my knickers, pulling them to one side and pulling firmly at my cock. She ran her hands up and down to the sheer material of my stockings.

Charlotte pulled her skirt up, so the strap-on dildo sprung up in front of me.

“Suck my cock!” she ordered.

I reached across and began masturbating her cock, taking the head into my mouth. As she had done before, Charlotte began fucking my mouth. This time she held my hair and head in her hands and pulled me further down her shaft, causing me to gag once more. There was nothing gentle about this and each time I gagged or choked, it just seemed to get Charlotte even hornier.

“Get my cock nice and wet,” Charlotte told me as she pulled my hair.

The dildo glistened with my saliva. Charlotte threw me a small tube of lubricant.

“Wank me,” she demanded.

I squeezed the lube into my hand and began to rub it over the entire length of the strap-on. I remember looking up at Charlotte and he eyes were full of complete and utter lust.

“Get on all fours,” Charlotte told me.

I was so turned on by her tone and how demanding she was being but as I turned around and got on all fours for her, I realised I was about to be fucked and most likely, fucked hard! I quickly used whatever lubricant I had left on my fingers to rub against my arsehole before Charlotte had a chance to start penetrating me. Charlotte pulled my knickers to one side and spotted what I was doing.

“Keep doing that,” Charlotte told me.

I rubbed the lubricant over my arsehole and then pushed a finger inside myself in an attempt to relax my spincter. Charlotte groaned her approval and I tried pushing two fingers inside. Just those two fingers felt tight and although I was desperately trying to loosen myself up it had the added effect of really turning Charlotte on, so she didn’t allow me much time.

I felt Charlotte’s hand push mine away and immediately felt the cock against my entrance. We had rehearsed a bit of a ritual over the last few months where Charlotte would begin by inserting the first couple of inches and then stop to give me time to relax before slowly increasing to the full six inch length. This did not happen.

The full length of Charlotte’s cock entered me, leaving my breathless. I fell against the bed, which seemed to annoy her and she pulled at my legs to bring me further down the bed. I tried to get back on all fours, but Charlotte had pulled my legs back so my feet hit the floor. Charlotte wasted no time and pushed my upper half back on the bed and pushed herself inside me once more. In this position I had nowhere to go and with my waist up against the side of the bed, Charlotte began fucking me and stretching my tight arsehole.

The pain didn’t last long and once my muscles had relaxed, it became as intense and erotic as the other occasions. Charlotte was a like a woman possessed and she was grunting loudly as she filled me up.

“You look so fucking sexy,” she told me.

“You should see your arse take my cock,” she said.

On future occasions Charlotte would video her point of view with her phone and show me afterwards.

My hard cock was resting against the bed and I couldn’t get my hand underneath to stroke myself. Every time I thought I had the opportunity, Charlotte would fuck me back down on the bed again.

“Oh god, I’m going to cum,” she shouted.

Charlotte often orgasmed when she was fucking me. She would say it was the feeling of having the base of the dildo bang against her clit.

Her thrusts became longer and deeper and her groaning became guttural, like a long loud moan. As the orgasm ripped through her, she began talking dirty to me. I had used language on her before and although she would swear during sex, this was the first time she had actually called me names.

“You fucking slut!” she called me, spanking my arse.

“Oh God, you dirty bitch!” she shouted.

“Fuck, I’m cumming so hard!” she yelled.

Each long slow thrust into my arse bought another profanity from her mouth.

She fell over me, the material of her blouse rubbed against my back.

She stood up and I turned around, laying on the bed.

“Masturbate while I watch,” she told me.

As she undressed, I pulled the knickers to one side and began to wank my cock. Charlotte soon stood completely naked but still with the glistening strap-on protruding in front of her.

She knelt over my legs and rubbed her cock as she watched me, as though we were masturbating for each other. It didn’t take long before I felt the familiar tingling in my toes, crawling up my legs and soon to be erupting in my balls.

“I’m cumming!” I shouted.

Charlotte moved forward and as I erupted, the jets of cum shot out over the dildo and my own hand and stomach. Charlotte scooped up any cum that hadn’t successfully landed on the strap-on and let them drip over its shaft. Charlotte then fell back on the bed.

“Clean my cock baby,” she told me.

I knelt up, still dressed in my knickers, bra and stockings and sucked the seed from her cock.

That night we seemed to fuck forever and it was the first time we ever pissed over each other, later that night when we were showering together. That was to be something else that would take on a life of its own and would galvanise our incredible relationship even further.

Our next step is to bring another man into our relationship and hope to share him in all ways possible. Charlotte desperately wants me to watch them fuck and then clean them both up. We recently thought we were close to achieving this when we managed two nights away in London, but unfortunately the other man lost his nerve and it didn’t happen.

What the last two years has taught me is that having someone to share your most innermost thoughts and fantasies with is the most incredible and enlightening thing imaginable. I know I could tell Charlotte anything without any fear of judgement and she knows she could do the same with me. I’ve also learned that many of the things we do give me pleasure from knowing how much it pleasures her and that just takes our relationship to a whole new level of trust.

She is truly an amazing woman.