We had arranged to meet at the Zetter Hotel in Clerkenwell. It was boutique style, not too big and had a well reviewed Italian restaurant on the ground floor. We both loved Italian food. It wasn’t cheap, about £200 for the room and £120 ish for dinner. It was to be our first night together. As using credit cards was out of the question I had salted away the money for the room over a period of a few weeks and Carolyn had withdrawn £150 from her personal bank account and had offered to pay for the meal.

We had arranged to meet at 5, time for some chilled champagne and hopefully a mind blowing fuck, then a bath together (the baths were enormous) a cuddle on the bed, which may again lead to sex, then get changed ready for our 8pm reservation.

I checked in at 4.30 and was amazed at the look of the room. I unpacked and put the still cold Laurent Perrier I had brought with me in the mini bar fridge. At 5.20 there was still no sign of Carolyn and I had received no text. At 5.30 I was getting a little worried and decided to open the champagne to calm me down. When I got onto my second glass it was 5.50. There was a knock on the door and opening it revealed a rather flustered looking Carolyn carrying an overnight bag and a very stylish black and gold carrier bag.
“Don’t say anything, I know” she blurted out. “There was this great sale and I just got carried away”
She began to look sheepish “I’ve done the most terrible thing” she said as she handed me over the carrier bag. I had no idea what was inside it but curiosity got the better of me and inside the bag was a box with the inscription Bottega Veneta on it. I opened it and nestling in cream tissue paper was a pair of brown leather peep toe pumps decorated with metallic floral stitching. They had a beautifully shaped thin round stacked heel which flared elegantly at the top. The heels must have been at least four inches in length.
“Well, have you just won the lottery” I smiled “They are absolutely beautiful but must have cost at least £400”
“£130 actually, in the sale, they’re an incredible bargain” she replied but didn’t look that pleased with her purchase.
“The thing is” she continued “I spent the cash that was going on our meal” At this she blushed which I would have found very attractive had I not been just a little annoyed.
“Bloody hell” I was not one for foul language unless it was used for talking dirty. Saying things like “ I want to fuck you so hard that you’ll remember it all next day” aroused me, and Carolyn as well, I like to think.
“I’m so sorry” she blurted out “I have no idea what came over me, I just wanted to look really nice for you and these shoes were so perfect”

To be honest, I wasn’t that angry, we could get some nice buffet food from the Marks and Spencer down the road with a bottle of Australian syrah and the room after all was beautiful, a place you could spend a lot of time in.
I sensed however that Carolyn was expecting me to be a little harsher with her and what came into my head was a fantasy I had had of giving her a gentle spanking.
“I think you ought to take your dress off and stand over there by the dressing table” I said in a sternish voice.

She looked surprised but obediently removed her beautiful floral print dress and walked over to the dressing table. She had on a set of brown lace lingerie which really accentuated her curvaceous figure. Below that was a lovely pair of sheer nylons held up with brown suspenders. I smiled to myself as I obviously realised that the shoes would have been the final touch and that she had probably considered having sex with me in that stunning ensemble. The brown pumps she was wearing were classy and elegant but no comparison to the Bottega Venetas.

When she reached the dressing table she turned with a quizzical look in her eye, but I think I also sensed a certain excitement in her demeanour. I knew I had made the right decision.
“Please turn round and bend over the table” I said, trying to sound stern. Again she obliged, offering up her beautiful lace covered bottom. I think she was ready for a spanking but not with the implements I had in mind. I picked up the new shoes and advanced towards her.
“£130, I reckon that’s 65 spanks to each cheek” I admonished, but as I think you bought them for my pleasure, I will be lenient, shall we say less than half that, maybe 30 on each side?”

I wasn’t sure what her reaction would be to this and I was surprised when she replied “That’s fair, I have ruined our first night together and I deserve to be spanked, but please don’t leave marks that my husband might see”
“I agree” I said “I will stop when both your arse cheeks have a little rosy glow, but you deserve to suffer a little pain”
She replied matter of factly “Of course I do, please start now”

Without her knowledge I silently removed the left pump and holding it by the heel administered the first spank to her left buttock. It wasn’t hard and she recoiled only slightly but she was surprised more than anything.
“Are you using my new shoes?”
“Yes, I answered, the left one for your left cheek and the right one for your right. Expensive shoes like this should be able to stand up to a little gentle spanking”
She laughed softly in an attractive girlish way “You are very resourceful” she said.
“Yes, and the punishment must be carried out, but before I continue I must check I haven’t left a mark”

I gently pulled down her knickers and ran my hand over those beautiful globes.
“No marks there, but I think I will have to leave your knickers at half mast so I can check on progress”

The next spank was with the right shoe to the right buttock which met with a gentle gasp but not a sound of great pain. I continued until I had completed ten strokes to each buttock and her cheeks were taking on a rosy hue. In the five minutes I had been spanking her she had never complained and I got the feeling it was turning her on rather than hurting her. Nevertheless I didn’t want her cheeks to get any redder.
“I need to stop now” I said “But I’m not sure you have had sufficient punishment for spending our dinner money”
“I agree” she muttered demurely “please do whatever you want with me”

I couldn’t ignore this invitation and knelt down behind her to kiss her reddened cheeks. Because she was offering me anything I was emboldened to part her buttocks and run my tongue around her beautiful puckered anus. She began to moan and uttered an “Oh yes”. This was hardly turning out as a punishment so I began to insert my tongue into her hole twisting it around and tasting the musky juices. Again she was getting even more turned on
“Fuck me there” she whispered in a hoarse tone

I had never had anal sex and was a little worried I would hurt her. When I mentioned this she replied that if I did it slowly there would only be a little pain to begin with which would be compensated by the feeling of fullness she would get when I was completely in. I had brought some lubricant with me, not because I was expecting to fuck her arse, but because a whole night of sex might have made us quite sore without something slippery to stop the rubbing. I now applied a good dollop to my forefinger and very gently pushed it into her anus up to my first knuckle.

“Is that OK?” I asked
“Mmm fine, push it in a little more” I obliged until my finger was almost totally up her bottom.
“Still OK?”
“It feels lovely but your finger is a lot smaller than your lovely thick cock” I sensed she was playing with me and I was incredibly aroused.
“Slip another finger in” she added. I couldn’t believe I was doing this but with some more lube my middle finger was now up to the hilt in her arse.
“I’m ready now” she whispered “Please stop if I say so”

I removed my lubed fingers noticing that their presence had left her anus slightly open. God, I was turned on. I quickly undid my trousers and let them fall to the ground. The sight of my blue stockinged feet however would have been a turn off if Carolyn had turned round so I decided to quickly remove all my clothes. Rolling on a condom and lubing up my very erect cock I moved forward to her reddened bottom but soon realised that our height difference (about 8 inches) would mean I would have to bend my knees to get full access. I had an idea.
“Put your new shoes on” I said
“What, now?” she replied, surprised
“Yes, they look like “fuck me shoes” to me and I would really like to fuck you in them”
“OK ……….master” (there was a hint of playful sarcasm in her tone).

She bent down to remove her shoes and I passed her the Bottegas. She very soon had them on and she resumed her position over the dressing table. Now, I had the most incredible sight. The shoes seemed to have slightly altered her shape and now her bottom was sticking out in an even more alluring manner. I moved forward again and this time my cock was beautifully lined up with her anus.
“Are you ready?”
“As ready as I’ll ever be”
“I’m just pushing in slowly, tell me if you want me to stop”

Obviously the preparation had been worth it because the head of my cock slid easily inside her with only a little coaxing. I didn’t know whether she had done this a lot before but she seemed adept and remained quiet as if concentrating (maybe bearing down is the right expression)
However when I was fully in everything changed
“Oh Joe, I love your cock in my arse, it feels so good, I feel full of you, start pumping me please”
“Yes I will pump you alright, I am so turned on, I want to really screw your arse. I want to fuck it hard”
“It feels so good now, you can fuck me hard, as hard as you like. Keep pumping until you come in my arse. I want to feel your cock jerking inside me…….ooh it’s so good”
“You’re so tight I don’t think I can last much longer, I’m coming!”
Come, my lovely Joe, I hope that has made up for your lost dinner”
“More than enough, oh yes, I loved fucking you up the arse!”

When I had ejaculated I was still so hot and wanted to return the favour. I slowly pulled out and removed the condom, which seemed fuller than ever of semen. Before Carolyn knew what had hit her I had her down on the floor on her back and I was lapping at her wet cunt like there was no tomorrow. She drew her legs up around my head and ground her soft pussy lips hard into my face. Within minutes she had the loudest orgasm I had ever heard from her (which, it almost goes without saying, was twice as loud I had ever witnessed from anyone, ever before) She was the most sexual being I had ever met and I would be eternally grateful that she had come into my life.