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Dear Diary

Category: Anal Sex
28.01.2021
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Dear Diary,

I am so embarrassed.

This morning, I went to the grocery store around the corner to buy some produce to make zucchini bread and sweet potato pie. While I was in the vegetable section, testing the firmness of zucchini, I noticed a presence next to me. I looked up and saw that it was Kevin, my neighbour. I hadn’t realized it but gauging from the expression on his face, it appeared that the way I was handling the zucchini was rather sexual. I was only testing to see how fresh they were, for goodness’ sakes.

Kevin raised his bushy brown eyebrows and laughed quietly.

I was so flustered with embarrassment that I quickly dropped the zucchini and left the store. I don’t know what I am going to do when I see Kevin again. I don’t think I could bear to look at him. What must he think of me?

2004-07-28

Dear Diary,

I saw Kevin at the Laundromat today. Why is it that just when I was pulling my wash out of the dryer, my thongs all fell to the floor right at his feet? It doesn’t help at all that I’ve been carrying a secret crush on him for months. He recently moved from France to my neighbourhood, as he explained to me the first time I met him which was at the café down the street. I was ordering a café au lait when out of nowhere, a French male voice said “no, no, no, you must drink coffee the proper way”. He changed my order to a small espresso, black. I protested, insisting that I must have my frothy milk and sugar, to which he replied, “you are creamy and sweet enough, you need black coffee to keep yourself balanced.” The audacity of this stranger, albeit a handsome one, with a gap in his front teeth just like Madonna, was unsettling but he disarmed me quickly with his confident charm. When the espresso arrived, he leaned up against the bar counter as if to ready himself to watch a performance. I felt so self-conscious and germane. I turned around slightly from his view to take a sip of my espresso. He was right, it wasn’t so bad but I still prefer café au laits.

“Well?” he asked.

“It’s good!” I answered, wincing inward at how lame and unsophisticated I must have sounded.

“See? Now you drink coffee like a true French woman!”

I could feel myself blushing as I finished the rest of the coffee in a big gulp.

“No, no, no,” he protested. “You must take the time to savour this coffee. What is all this rush?”

“I don’t know, that’s just how I drink.”

“Ah, ah, ah,” he wagged his finger. “You must learn to slow down and enjoy the simple pleasures in life, for they are far and few in between, n’est ce pas?”

“I suppose.” I am doing it again! Being lame.

Now that I had drank my coffee so quickly, so un-french-like, I felt as though I had no recourse but to excuse my small-town self from his oh so French presence.

“Wait, what’s your name?”

“Emma, you?”

“Kevin.” The way he said his name, the accent was on the “vin”, oh, how so French. I always thought Kevin was an English name. It sounded funny with a French accent. But I liked it. I smiled at him briefly and left.

And now, all those months of bumping into him randomly at the Laundromat, at the café, at the grocery store had built up my secret crush on him. He seems so sophisticated, so worldly and cultured. He has a perpetual tan, even in the deep of winter, and he has such nice European clothes. Even his metal wristwatch seems French. But I don’t think he knew. I am not sure he would be interested in a naïve girl like me. I am rather conservative, quite shy, all my clothes are from the Gap, and I prefer books to drinking or partying. I tape all my favourite soap operas so I can watch them when I get home from work and when I’m feeling sad or lonely, I like to put on my Holly Hobbie bonnet. No one knows about this, of course. About both the soap opera tapes or about the bonnet. I would be mortified if they did.

Anyways, back to the thongs at Kevin’s feet at the Laundromat.

Sigh. You know, I only bought those thongs at the insistence of a sales girl who disapproved of my panty lines when I tried on a pair of black pants at BCBG. She cowered me into buying them, I swear! I am not the sort of girl who would ever buy them just like that, I was pushed into it. That day, I brought them home, washed them of course and then tried one on. It felt so weird, this string of fabric stuck in my bumbum. I had to keep resisting the urge to pull it out. How do girls wear them? But I forced myself into wearing one with the black pants I ended up buying when I went to work. I am so sure that everyone at work could tell I was wearing a thong. I hope they didn’t think I was being slutty. I wouldn’t be able to bear it if they did.

And now, here they were on Kevin’s feet. All I wanted to do was disappear off the face of this earth. For sure Kevin is going to think I am some brazen street walker. I just wanted to run home, put on my bonnet and hide in some dark corner. I could feel my face getting so red, and tears beginning to spring to my eyes.

“Ah, er, uh…” I mumbled as I quickly bent over and swept them off his feet, dropping one. WHY? Why do these things always happen to me? Am I doomed to perpetually embarrass myself for the rest of my life? I was temporarily frozen in place as I stared at the fallen thong. Kevin bent down and picked them up from the floor. “Such a beautiful color.” he was referring to the thong which was fuchsia. I actually wanted to get a white pair but they didn’t have any left in my size which was medium. So I got fuchsia instead, and rather reluctantly, I might add. Although the matching bra was pretty nice, it was simple and conservative, just the way I like it. It suited me perfectly. Besides, the colour matched the flowers I was growing in my little garden at home.

I couldn’t look at him in the eye. I just shoved my entire laundry into my bag and as usual, fled.

200407-31

Dear Diary,

Saw Kevin at the café this morning. I tried to pretend that I didn’t see him but to no avail. He came up to my table and asked if he could sit down. Remembering that this man saw and touched my thong, with its uncomfortable fabric that wedges itself in my bum, I could barely bring myself to say loudly enough that indeed he could.

He sat down and pulled out his pack of red Gaulois. “You smoke?” he asked, offering me one.

“Oh no thanks, I don’t smoke,” I demurred.

“Good for you, it’s a terrible habit, smoking.” He wouldn’t stop staring at me. I was too shy to look at him straight on so I looked everywhere, pretending to absorb the scenery. I did notice how he took out his matches and lit up his cigarette, cupping the flame in his palm. Even the way he did that seemed so French. It made me all the more aware of how different I was from him. I felt so dorky and plain.

“You have green eyes!” he exclaimed. The sunlight that was filtering into the room slanted across my face, my eyes which usually appear brown always turn vividly green and copper in the light. “Oh! They are so lovely!”

I blushed, typically. I couldn’t let go of the memory of the fallen thong incident so it was all I could do to force myself to reply, “thank you”.

Kevin leaned forward, placing his elbows on the table, to look into my eyes. I tried to look away but he put out his hand on my face to gently turn it back to him.

“You are very pretty,” he said quietly.

I shook my head, unable to accept his compliments. I am not good at things like that. Compliments, I mean.

“Yes, you are,” he insisted, smiling widely. “But of course you know that, certainly.”

I shook my head again, looking down.

“Oh, come now,” he chided.

I still couldn’t look at him.

“May I ask you a question?” he asked.

I nodded.

“Have you ever been to Alistair’s?” Alistair’s is a restaurant that was a few blocks away, I had walked past it many times, but had never given it a thought for its menu, posted on the front window scared me off with its double and triple digit prices.I couldn’t even recognize the names of the meals, they all seem so foreign and strange. I would never fit in a place like that or would a place like that fit into my budget. Anyways, I don’t eat in public places alone. I’m not that brave.

I shook my head no in reply.

“Ach!” he sat back in his chair. “You must come with me one night. What are you dong this weekend?”

Uh, doing my laundry, maybe buy some more plants for my garden. “Um, I haven’t decided yet, why?”

“Why?! Because you must come with me to Alistair’s, I insist!”

“I can’t afford to go to places like that.”

“Ach, but it’s my treat, I would pay anything to spend a couple of hours to look into those eyes of yours.”

Now I knew I was blushing. My entire face felt as though it was on fire.

“Well, all right, I guess.”

“Excellent, Then I shall come pick you up at eight.”

At eight? Do French people eat that late? Oh my.

“Okay.”

He had such a big smile that I couldn’t help smiling back.

2004-08-01

Dear Diary,

I’m a changed woman. No, correction, I am now a woman. I am really really a woman. Last night was a night of many firsts. First time I’ve ever been to a fancy restaurant with a man, first time I ever had a cocktail drink, first time that I’ve ever…

Let me start at the beginning of the date at Alistair’s.

First of all, I really didn’t know what to wear to such a restaurant. I had emptied out my entire closet trying to figure out what to wear. Luckily, I came across a dress that my sister left behind last time she visited me. It was a clingy black dress with spaghetti straps. I remembered when she made me try it on that she said that I was so lucky to have such curvaceous hips for the dress made me look like I actually have an hourglass figure. I decided to trust her judgement and wear it. But it was so clingy that I knew that I would have to wear the dreaded thong. Remembering that Kevin liked my fuchsia one, I put that one on in addition to its matching bra. I felt so terribly naughty wearing it that even alone in my bedroom, I felt rather self-conscious.

But what choice did I have? None! All my other clothes were faded Gap clothes, not at all appropriate for such a date.

I found a pair of flamenco dancing shoes that I had bought one time for Hallowe’en when I dressed up like a Gypsy. It was bright red and patent leather. After I assembled my outfit, I took a look in the mirror and could hardly recognize myself. Who was this person? And what would Kevin think? He’d never seen me dress anything close to this before. I’m usually pretty dowdy.

I was rather overwhelmed by the sex vixen image I saw in the mirror and decided to put on only black mascara and red lipstick. Any more makeup like that and surely I would be arrested for streetwalking.

Just when I was taking one more unsure look in the mirror at my outfit, the doorbell rang. It’s Kevin, he was here. Oh goodness, I had hoped that I looked all right. I was actually starting to think that perhaps I shouldn’t answer the door, maybe I should just pretend I wasn’t home. I was absolutely terrified to answer the door, look at how I was dressed! I could barely stand to look at myself for pete’s sakes.

Very very reluctantly, I forced myself to walk down the hallway to the door. My legs were shaking and my hands were starting to sweat. I had never been so nervous in my life.

I opened the door.

I will never forget the look on Kevin’s face. He looked so shocked and yet so pleased. As soon as I let him in, he grabbed my hand and gave me a little spin. It was so lovely, he really made me feel like I was really pretty.

“You look absolutely stunning,” he said after I’ve finished spinning. “I’m so lucky to have you for my date tonight.”

I could tell he meant it and I adored him all the more for it. He didn’t look too shabby himself. He was wearing a pin stripe suit that was toned down by a tshirt and Diesel sneakers. It sounds like an odd combination when I write it down but really, it really made him look so good. The white tshirt with the black suit really showed off his tan and made his teeth look pure white.

The sneakers he wore were red with sporty stripes. I liked that we both were wearing black outfits and red shoes. It comforted me somehow.

“Ready?” he asked.

“Very ready,” I giggled. And immediately felt silly for having giggled.

We walked out into the cool summer evening, and Kevin took my hand. It felt so nice to feel his warm hand covering mine. It immediately made me feel much more relaxed and comfortable. I looked at him to give him a smile. He smiled back and gave my hand a little squeeze.

People were actually looking at us when we were walking toward the restaurant. I had never been looked at like that before. Some of them even turned around to take a second look. I felt as though I was on top of the world.

Soon enough, we arrived at the restaurant, which was spartanly decorated as if not to steal the show from the food. The walls were creamy white, the furniture were dark stained modern furniture and the tablecloth matched the walls. Glass bottles of all sorts of shapes and sizes lined the shelves on the wall, lit up by inset light that were embedded on the floor along the baseboards. All together the décor made me think of an art gallery that one might find in Chelsea, New York.

Kevin pulled out my chair for me to sit down. What a gentleman.

As soon as he sat down, a waiter hurried over with some menus. They spoke in French rapidly, leaving me entirely impressed and confused.

“I’ve ordered a bottle of wine for us,” Kevin explained after the waiter left. “I’ve also take the liberty to order our meals.”

I was relieved that he did that, I would have had no idea what to get.

Within seconds, the waiter came back with a bottle of wine and poured it into our glasses.

“To a wonderful evening,” Kevin held up his glass. I held up mine and we clinked.

“I can’t believe how beautiful you are tonight,” he said.

And this time, I believed him. The way he said it, the way he looked at me, I know he was telling the truth.

“Thank you,” I replied gratefully.

Kevin reached across the table to bring my hands up to his lips.

I could only stare in fascination. That he was actually kissing my hands with his beautiful full lips. I closed my eyes to savour the sensation. When I did so, I felt one of my fingers slide just a little in between his lips.

I was shocked!

You have to understand, dear diary, that I had never been on many dates and certainly had never been on a date like this one with a man like Kevin. All of that was overwhelming enough but now this, Kevin sucking on one of my fingertips. I tried to play it suave but Kevin chuckled, I didn’t fool him at all.

“You look so delicious that I couldn’t resist taking a taste of you,” he said, the candle on the table made his deep brown eyes sparkle like amber.

“Ah, er…” I mumbled. I decided that I rather liked how it felt, the way he kissed my hands. Certainly I had dreamed of being on a date like this with Kevin long enough, why not just enjoy it?

I relaxed and let him hold onto my hands. I looked around the restaurant and a couple caught my eye. They were much older, in their fities, and very well dressed. The man held up his glass and gave me a nod. Somehow he could tell this was a special night for me. I nodded back and looked back at Kevin.

He was massaging my hands gently, and once again, brought my fingers to his lips. I licked mine in anticipation.

He took my index finger and placed it directly between his lips. Then slowly he began to suck it in until I could feel it touching his warm wet tongue. It was so sexual that immediately I could feel my entire body fill up with heat.

I grabbed a napkin with my free hand and fan myself slightly. I was truly becoming rather hot.

Kevin laughed, my finger still in his mouth. I could feel the vibration of his laughter transferring from his tongue throughout my finger. By this point, it felt as though I was dissolving into a mass of liquid.

The waiter returned and Kevin slowly removed my finger from his mouth while the waiter, well, waited.

I couldn’t believe Kevin would do that in front of anyone at all. I quickly looked at the waiter who was smiling. He gave me a wink.

I had been so shy and nervous when we first sat down that I finished my drink quickly. The waiter refilled my glass and left.

I crossed my legs, one of which brushed up against Kevin’s. He looked at me and smiled while he let one of his hands slip down underneath the tablecloth. His warm fingers began to stroke my leg that was over the other. “Your skin feels like butter,” he murmured.

Come on, make like butter, soft and easy to spread – that song from Detroit Grand Pubahs began to play in my head.

I couldn’t speak. I was entirely in Kevin’s spell. Of course I am sure the red wine was making me more pliable to his ways.

“I want you to do something for me,” Kevin whispered.

“Wh-what?” I could barely get out the words.

“I want you to sit next to me.”

I didn’t know if I could do as he asked. My legs were boneless at that point but I tried to get up. The waiter returned, moving my chair closer to Kevin so that I was no longer sitting across from him but now sitting right next to him.

The waiter left.

Kevin brought his hand back down under the tablecloth again.

I could feel his hand first on my knee, stroking it gently but firmly. Then I could feel it slip beneath the hem of my dress.

“What are you doing?” I gasped.

“Shh…”

Holding my eyes with his, Kevin moved his hand further up underneath my dress. I clenched my legs tightly together, relieved that there was a tablecloth to hide his actions.

The waiter returned with the appetizers, which were lamb chops and salad with lentils. At first sight, they seemed rather humble. Kevin reached for a chop, picked it up by the bone and told me to open my mouth. I looked at him to see if I could trust this man, to see if he was playing me.

“It’s ok, I won’t hurt you,” he promised, his teeth gleaming white as he smiled.

I let my lips part ever so little.

“Open wider.”

I opened my lips a little more. As the lambchop entered my mouth, I could taste its infusion of apple glaze which alone made me swoon but at the same time, I could feel Kevin’s hand moving up between my legs, forcing them apart. As I chewed the lambchop, I could feel his fingers reaching the edge of my fuchsia thong.

I gulped.

“Take another bite,” he encouraged. I gulped down another sip of wine and opened my lips again. Kevin brought the chop to my mouth and as I was about to take another bite, his fingers slipped beneath my thong and I could feel them becoming wet with my escalating arousal. He slipped a finger into my virgin vagina and whispered into my ear, “you feel so good.”

I did feel good. And appalled. And yet sooooooo good. It felt good to let him take control. To let him force me out of my prudish tendencies. It felt as though he was giving me release from myself which I hadn’t realized I needed until that moment.

And all the while, his finger moved in deeper until his thumb was touching my clitoris. I just about jumped out of my chair from his touch. It was such a surprise because I wasn’t prepared for how fabulous it felt to eat this divine lambchop and being finger-fucked at the same time in a beautiful restaurant.

“Ohhhh…” The waiter had returned and heard me make that noise. “It’s good, isn’t it?” he asked referring to the appetizers.

“Ohhh, it is very good,” I replied, being bold now that I have wine coursing through my veins and a gorgeous man’s finger inside my cunt.

The waiter promised to return with the main courses soon.

“I can’t believe you!” I said to Kevin to which he chuckled. “Are you enjoying yourself?” he asked rhetorically.

I nodded shyly.

He took his finger out leaving me feeling empty and a bit cold. I looked at him to see why he pulled away. He brought his fingers to his lips and began to lick them as if they were sticky from the sauce of the lambchop. He slurped his fingers with such greed that I was sure my desire was going to seep through my dress into the chair.

The waiter returned with the main courses which were grilled octopus with eggplant caviar and market fish wrapped in vine leaves.

“Here, let me serve you,” Kevin said.

He pried apart the vine leaves ever so carefully revealing the flesh of the fish inside. He took a fork and picked up a bite. Once again, I opened my lips to receive his offering. Without realizing it, I had opened my legs too. His hand came back, his finger came back inside my vagina, stroking me inside, his thumb rubbing my clitoris as he fed me. I have to tell you, the combination of the two was sheer ecstasy.

Then he picked up a piece of the grilled octopus with his fingers and fed me. His finger pulled out and began to move downwards. I clenched my legs, not wanting him to touch my dirty spot.

“Open up,” he commanded.

I looked at him pleadingly, willing him to understand that I couldn’t, nice girls just don’t do things like this.

“Come on, open up,” he repeated.

Reluctantly and petulantly, I let my legs relax and open a little. Kevin picked up another piece of the octopus and said “open up wide.” I stared at his face, taking in the beauty of this man, and of his masculinity. I complied, I opened up ever wider. His finger moved downwards a bit.

“Sit on the edge of your seat.”

By then, I was totally in his spell. I moved closer to the edge of my seat and waited. As Kevin continued to feed me, his finger, wet with my sopping arousal, began to tickle my anus.

I almost choked on the octopus. “I can’t do this!” I whispered almost hysterically. Kevin looked at me with kindness and whispered back, “it’s all right. You have my word that I won’t hurt you.”

I took a deep breath, finished my fourth glass of wine and kept still.

His finger, still resting lightly on my anus, began to circle it again, sometimes stroking it. Then he would return it to my vagina as if to I were a dipping sauce.

Then he would bring his finger back again to my anus. I couldn’t bear to look at him, I felt so dirty, especially because as much as I could never say it out loud, I really did like how it felt. But it was so wrong! I was being such a bad girl.

“I want you to feed me,” Kevin said. Picking up my knife and fork, I began to cut his food. As I was about to give him a bite, his finger started to push into my asshole. I was so ataken back that I held his bite of food in mid-air.

“Go on, feed me.” Trying to collect my senses as best as I could, I placed the food into his mouth. As he chewed his food with audible pleasure, his finger pushed even more into my asshole until I could feel it filling me up. I was torn between two desires, one to pull away, one for Kevin to push his finger inside even more.

I looked up, aware for the first time since we began eating that we were in a public space. I caught the eye of the couple sitting across from us. This time, it was the woman who smiled knowingly. She knew exactly what was going on. She turned to her husband and said something. He looked at me too and nodded with a grandfatherly smile. “It’s all right,” they seem to be saying.

I looked back at Kevin, aware of his finger now pushing in and out of my asshole. “Keep feeding me,” Kevin said, his breath turning into a slight pant.

I could feel my own breath echoing his as my lips were swelling up and my clitoris hardening. I was now pre-orgasmic.

Placing another bite of fish on his fork, I fed him, trying not to make any noise while his finger fucked my bum and his thumb stroked my clitoris. “Please stop,” I begged him.

He didn’t say anything, just kept going, I was imprisoned by his finger, impaled literally upon it, unable to get away until I was released and released I was finally for within minutes, I was exploding with orgasmic sensations, my ass milking his thumb as it squeezed and relaxed.

“Oh my goodness.” That was all I could say when the waves ebbed.

Kevin slid his finger out slowly.

“Waiter, the bill, please,” he called out while he held my hand with his sticky one.

He walked me home, holding me up slightly for by then, my legs were weak, his arm wrapped securely around my waist.

He kissed me on the front steps, our first kiss.

Then he bid me good night, making me promise to go on another date with him next week before he left.

I can’t wait, dear diary.

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