u/Writing_stuff332

Hey there my fans and smut readers. This is the second story of a trilogy where I remember my three most memorable things I did with an ex once. This one my not be that special as the first one (red: the anal experience), but to me it was memorable because of the sexual intensity. Hope you enjoy!

It was a beautiful summer afternoon. It was getting late and we were walking around hand in hand. Talking about nothing and everything, just having a great time. Yesterday we had a fight, about what I cannot remember but we met up just to talk it out.

As any young couple does, talking it out means actually fucking it out. So we already had two rounds done before we went on our walk. We decided to go on a walk because we could hardly stay in bed all day, we always do that.

So it was in a park, a beautiful park, not too busy, not too quiet. But as we were walking around the mate afternoon sun was starting to set and afternoon turned into evening.

I wore a white linnen shirt, which was a bit see through, black denims and white Air Force sneakers.
Chiara slipped into a top she had since she was a young girl. But at her age her breasts were actually very very revealing. It was a white tank top with AC/DC on it, further than that she wore a jeans short. One of those slutty jeans shorts, I have always loved them. How that type of short shows a little bit of her ass. Everything jiggled with every step we took on our walk. Every man we passed could not help but stare.

I did not mind, I would stare too, but I was actually lucky to see everything and feel everything.

She looked stunning. Her hair was waving in the wind, she had her biggest smile. I could see she was enjoying her time. As we walked up to a bench which had a lookout on the lake we sat down.

“Look, I’m sorry for being so rude to you earlier, I did not mean that.” I uttered
“That’s fine, I was a bitch too.” She said as she layed her head on my shoulder.
The orange sky was glowing on her skin giving her a light orange colour.
“We made it up anyway baby” she continued. “And you did not dissapoint.” She said smiling as she gave me a little kiss.
“Well you were also quite feral if I can say that.” I said jokingly.
“What do you mean?” She asked shocked
“Well, I have never felt you ride so wild to be honest.” I admitted.

She blushed and bit her underlip.
“Well, when it feels so good, wouldn’t you?” She asled as she was caressing me through my long hairs.
“I have proven I can go really hard, don’t you think?” I said with a wink.
She whispered “oh you have baby, you have. I love it when you fuck me like that.” She said.
“Yeah?” I asked.
“Yeah I do, I mean don’t get me wrong, I love love-making. But sometimes I just want to be fucked you know?” She said with a little giggle.
“Oh in that case, I think there’s a round in the chamber still.” As I gave her a kiss.
“Is there?” She said as she started kissing me passionatly.

I felt her soft and wet lips on my lips. They were dancing a dance of passion and seduction. I felt how we slightly let our tongues join in this dance. They were touching each other slowly. I felt her hands on my chest, one hand on my sidebody going over my pants.
Meanwhile I hele her hips and occasionally slipped over her large breasts. I noticed her nipples were hard. I held one breast firmly in my hand and massaged it to let it drop down. It jiggled.

After we stopped kissing she smiled at me.
“Phew.” I said. “Yup, definetly ready for round 3.” I said jokingly. I felt how hard my cock had become and it was getting thight in my pants.

“Shall we go fix that third round then?” She asked as she went over my bulge with her hand.
“Uhm, sure but this guy has to calm down first.” I said pointing to my cock.
“Oh my, did I do that? I’m so sorry baby.” She said sarcastically.
“Uhu? You’re sorry? You knew damn well what you did.” I said laughing.
“Well how long is it gonna take?” She asked as she leaned forward so I could look inside her cleavage.
“Honestly, hours with you sitting here like that.” I admitted.
“Oh like this?” As she bend over a bit more.

She giggled.
We heard some voices in the distance and it was a little family. We nodded, said hi, and they went on.
“Oh but it will be dark soon.” She started.
“Yeah, I’m really stuck here.” I said.
“Well” she started as she looked around.
She came up to my face and whispered in my ear “maybe I’ll have to solve it here.” As she gave me a tongue neck kiss when she went over my bulge.
I let out a small moan. “Really? Right here?” I asked shocked.
“Uhu” as she gave me another tongue neck kiss. “I know you. You need to cum before we can go baby.” She said teasingly as she unzipped my pants.
“What if someone passes by?” I asked breathing heavy and looking around.
“Well baby, then I will have to find a way to make you cum fast huh?” As she put her fingers in my open zipper. I felt how the tips of her fingers went over my underwear.
“Omg baby, why’s it so wet?” She said as she kept caressing.
I already let go alot of precum.
“Because of you.” I said as I grabbed her tit again and massaged it.
“Mmmh, but I don’t have a problem baby. People look at me anyway. It’s you.” She said as she oushed her hand in the opened zipper to fully grab my bulge.

I was considering. I mean she could make me cum now and then a last round when we get back home.
I brought my face close to her ears and whispered “do it quick then.”

She looked at me, smiled, bit her lip. She brought her hands to my button but before loosening it she sat quiet and looked around.
“All right clear.” She said. She looked at me. As she was opening my pants her breasts were moving with her arms.
My underwear appeared and you could see a wet stain on it from precum.
She smiled at that sight. “Omg baby, you were so horny?”
I nodded.
She looked around again. The sun was beaming her orange rays on her. I could make out the contours of her entire body.
All we heard was tsjirping of birds and the crickets. Nobody in sight.

She proceeded to lift up my underpants and grabbed my cock. It throbbed inside of her her hand. She smiled. “Oh baby, let me take care of you.”
She pulled my underwear up and a bit down. My hard cock was veiny, the tip was shining from the precum. She let it stand upwards and first touched and massaged my ballsack. Clean shaven, with her touch it felt more amazing. I felt how she was putting a bit of precum on her hand and she proceeded to grab my cock fully. Using it a bit like a lubricant.

She looked around as she started to go up and down slowly. Each time she went down on my cock with her hand she pulled my foreskin down to. Her palm landed on my ballsack. It exposed a shiny and slimey tip.
“Oh my god” I moaned silently.
“You like that baby?” She said as her breasts were jiggling on The same rhythm with her stroking. She leg loose, looked at me, gave her hand a lick and then proceeded. She made some twirling twist movement with her hand. It felt sensational.
I laid back on the bench and every stroke was an intense feeling.

“I want you to cum for me baby.” She said. I felt her tits again. She increased her pace, alongside came the sound of a wet cock getting jerked.
“Are you there yet?” She said.
“No, totally not.” I moaned.
She stopped jerking. Listened to the surrounding area. Nothing changed. She grabbed my cock again and whilst she was on the lookout she jerked slowly again.
I felt how all of my cum was building up.

“Fuck it, I need to speed this up.” She said as in a swift mood she brought her lips to the tip of my dick. I felt how she kept them there, the tip of her tongue was teasing the bottom side of my tip which was extremely sensitive. In the meantime she was jerking again.

“Oh fuck, yes, like that baby.” I moaned. She kept stroking, licking. With every lick I arched a bit.
“Almost there baby.” I moaned.
I pulled her from my cock.
“Like this?” She asked.
I nodded and sighed.
“Cum for me baby, I want you to let it all out.” She said.

As she brought her lips down one last time it took 2 or 3 strokes untill I let go and explosion of cum.
“Fuck, fuck, yes, yeeees, oh fuck” I moaned as I was cumming all in her mouth.
She pulled her head of my cock and while she did that she got a bit of sperm squirted on her face.
It landed all over the grass an the bench. Squirt after squirt of cum. The last one ended in her cleavage.

I sighed with relief. “There we go baby.” As my cock went down.
“I swallowed a bit of it. You needed that.” As she gave me a kiss.
I looked at her and a bit of cum was on her forehead and dripping in her cleavage. She smelled of cum.
I gave a tissue and we cleaned ourselves up.

“Mom made dinner, we gotta go home.” She said.
I looked back and saw all of my cum on the grass.

I occasionally walk by that said bench in the park, with it’s pretty little lake. And I think about that evening.

This happened during the covid break-out. I was also in a relationship at the time. I still am. This is the story of me, who was 22 at the time, and my coworker Karen who was 43.

I landed myself a job at this firm. I was the administrative backbone of checking up members who were boarding ships.

I went to the head office, which was a good 1,5h travel using public transport. Got back home, and made sure everything was in order. I received an e-mail from a certain ‘Karen’. She introduced herself as she was gonna take me under her wings, train me, and ensure I was capable of doing my job correctly.

The next day I got on a Teams-call, those horrible Teams-ringtones give me PTSD nowadays, but then I was discovering workplace dynamics. It was Karen. We did not call with camera, just a call. I heard her voice at first and I found that it was a soft, sultry, and very elegant voice. She showed me the ropes and I quickly caught on. We worked in a team of about 6 people. She was number 2, I was just an employee.

After about a month, a month and a half, I actually had a say in the team. I made reports, followed meetings, supported Karen when needed, or the teamlead, and even showed the ropes to the new personnel.

In comes Carolina. She couldn’t follow at all. Karen explained everything multiple times and still she did not understand the job. I was working and I got a call from Karen who was sounding desperate. “I’ve hade it. I am seriously doubting myself if it’s me.” She started.
“What’s wrong?” I asked.
“Carolina, she’s been with us for a couple of weeks and still doesn’t understand the basics of what we do. It’s getting frustrating and I don’t want to work it out on her.” She said
“Look, I’ll have a go and see if I can teach or train her. And I will report back to you.” I replied.
“I would be so thankfull if you do that.” She said

So I did as I said. I trained Carolina. But every time she forgot small details. Or she had a black out. She was anxious about losing the job. I reported her progress immediatly to Karen and our boss. I was honest that Carolina actually made a small amount of progress, but it will have to take alot of time for her to fully grasp the entire scope. I got a thanks from my boss and he and Karen were in a meeting.

The next day Karen called me and she sounded sad.
“We decided to let her go.” She started. “But I was the one who had to bring the news.”
“I can imagine that mustn’t have been easy for you. First time?” I asked worringly.
“When they start crying it’s just not nice you know?” She said.

I stayed and we ended up talking alot. This was a long day. Not because of the amount of work. We actually clocked off but stayed chatting for a couple of hours on end. There a click was made. It was friendly, but somehow it felt more than friendship.
She told me about her personal life. Her daughter and son, both younger than me. Her recent divorce. The construction in her street, every day stuff. I told her how I still lived at home with my parents, had a girlfriend, talk about my previous job.

After we logged off I could not stop thinking about her. I like the idea she didn’t too, as I would come to find out.

And like that every week we closed off with a long chat-session. Gossipping about co-workers, telling each other life-stories. I was telling her how my previous job, a call centre, was basically one big weird place. Many people were seeing each other after work, inappropriate work ethics, affairs. She told me she knew as she worked in a call centre too.
As we were chatting she proposed “look, I can see your picture, but why don’t we turn on our camera’s? It’s covid and I don’t think bars and such will open soon so we can have a drink as colleagues.”
“Sure! Good idea.” I said as I turned on the camera.
She turned on hers.

I saw a beautiful woman with darkbrown hair, light brown eyes, smaller lips, white smile and her face was very white in the light of her screen. I saw that she wore a white tank top and a sweater as it was an unusally cold spring day. I couldn’t make out the rest really good but I imagined she had around a c or d cup with her slimmer body.
“Here I am! Finally we see each other!” She said.
“Indeed! So nice to finally see you!” I told her.
“Sure, it’s much nicer to talk to you this way.” She said.

From that point we chatted with camera on.

Enter the summer

Come the summer Karen and I had developed a personal friendship. Occasionally a dirty joke was told. Lot’s of laughs, alot of work too. I showed a picture of my girlfriend and she showed pictures of her kids.

In the middle of July a heat wave struck us. It was relentlessly warm for four weeks. Our conversations were increasing in two to three times a week of chatting. Even though I had a girlfriend some light flirting was there. Compliments as “you look good” or “you’re a catch, anybody would be happy with you” from my end, as she usually said “well your girl is a lucky one”.

This particular friday was a bit different. I have been fantasizing alot about her, masturbating to what she would look like. I was masturbating right before our call thinking about her body. Her pink nipples on her breasts. How she looked wet and sweaty. How it would be making love to her body.
I felt myself climaxing and a small load of cum squirted all around. I was sweaty. And right after that Karen called. I picked up.

“Hi there, oh my good you’re sweating! Have you been working out?” She asked
She was wearing a horizontally striped and thight tank top. I saw she had a red bra on because the strips were kind of small. She had a visible cleavage that was rather deep. Which I did not mind.
“No, I’m just really hot today.” I replied, in my mind I was telling her that she should have known what I was doing. I looked down and I saw the small cumstains on the floor.
“It’s unbearable today. Usually I can handle heath but today is an exception.” She said as she was wappering her hand to her face.

“You don’t say” as I zipped up my pants subtely.
We got chatting. And as we passed on the subject of work we got to being home alone. She told me her kids were away on holiday with their dad. She had the whole house to herself. I said my parents were gone for two weeks.

“I love being home alone sometimes” I said. “I can do what I want, eat and drink what I want.”
“I totally understand you, I’m glad I can have some me-time. Don’t get me wrong I love my kids. Sometimes I just need some time for myself.” She said.
“I understand. Life is hectic enough.
So you can actually relax this week?” I said.
“Absolutely!” She replied.

I thought about something and I just said it.

“Hey you know bars are still not open.” I started.
“Yeah.” She said questioningly.
“What about we pour ourselves a drink and pretend we are at a bar?” I asked.
“That’s actually a great idea! I’ll stop working now, too hot anyway.” She said

We both unplugged our pc’s and took them to our kitchens. I poured myself a glass of red wine, she poured in a white wine. We said cheers and started drinking. And as the drinks were flowing, so the conversation was getting more unhinged and direct. Mostly towards a sexual way.

“So how is the divorced life?” I asked
“Oh it’s nice, but lonely. You’re lucky. You have a girlfriend you know.” She said as she took a sip from her wine. I noticed how she got tipsy. I myself was also a bit dazed.
“I know, bit honestly we don’t see each other alot. She has a busy job.” I said as I poured some more wine in my glass.
“Oh, oh that’s sad. At your age I met up with my boyfriends continuesly.” She said. “I couldn’t wait to see them, and feel them.” She said laughingly as she was running red.
“Karen, you get me!” I replied. “I sometimes miss her body if I’m honest.”
“Which is normal. You’re a young, and handsome guy. You have needs.” She said with a smile.
“That’s true, but I’m sure you do too. It’s not that you’re in your 40’s that it stops.” I said.

She looked at me for a second.
“You’re pretty bold when drunk, I must say.” She started.
I felt like ‘shit hit the wrong nerve’
“I like that” she said with a teasing smile and a wink.
I felt the room getting intensly hotter.

I felt I was sweating. It was visible on the computerscreen and in my t-shirt I was wearing.
She noticed.
“My God, are you okay?” She asked worringly
“I’m fine, it’s just so warm today phew.” I replied whilst waving my shirt in the hope of cooling down a bit.
“I can see it, look even I’m sweating!” She said as she pointed to her forehead. Her darkbrown hair were always in a ponytail. I liked that about her.
“I can see that, well for me it’s my entire body.” As I said whilst taking another sip of wine.
“I hope this one helps me to cool off for a bit.” I added.

It didn’t, but it did make me horny, and unhinged. And it seemed the white wine had the same effect on her.

“I mean.” She started slowly as she played with her ponytail.
“What?” I asked curious
“Well, if you’re that hot, you can just lose your shirt if you want.” She said as she took a sip.

I fell silent. I did not expect it, only fantasize about it.

Without saying a word I put down my glass and I slowly took off my shirt. My sixpack was visible and muscled chest too. All though it was wet with sweat. It was slowly dripping over my body in the sultry evening light.

I sad how Karen was looking. She was giving her eyes a great look, enjoying all parts of my body. I could see in her eyes she got what she wanted.

“Enjoying the view?” I asked teasingly as I hung up my shirt whilst visible in the camera.
Karen stayed silent, almost drooling until she snapped back to reality.
“Uhm, oh, yeah yeah, I’m fine. Good, yeah.” She said as she was a bit out of focus.
“You’re not huh?” I said
“I didn’t expect that in all honesty.” She said as she started waving her hand to her face.
“What?” I asked
“Well the strip tease right in front of me.” She said “and also I did not expect your body to be so fit.” She added.
“Hey look, do you enjoy it?” I asked
“I sure do. Such a fit body, gosh.” She said.
“Thanks, you can feast your eyes.” I said.
“I certainly am.” She said as she brought her head towards the screen and leaned her head on a hand.

“What would your girlfriend think that you were showing off your body to an older woman like me?” She asked
“In all honesty, does she have to know?” I replied
She smiled and took another sip of her wine.
“You’re a bad boy.” She said smiling “but no she does not.” As she winked.

“My bottle is running empty.” She said as she grabbed it.
“I think i have another one somewhere. Can you hold on a second?” She asked.
“Sure. I can get a refill too.” I replied.
She dissapeared and I grabbed a small red wine bottle.
It took a good ten minutes before she reappeared.
Something was different.

In the dim light I directly noticed that her bra straps were gone. Her breasts were more saggy and dangling as she sat down. She poured herself another glass and I could just make out her nipples in her top. ‘She got rid of her bra’ I thought to myself.

We cheered. I was the one who had a hard time focussing. And she seemed to like it. I caught myself staring at her breasts. They were beautifully saggy, her nipples were hard and visible, and with every movement they were juggling and wiggling a bit. I was mesmerized with that beauty. And happy she took off her bra.

“Are you doing okay now?” She asked teasingly as she was onto me.
“I sure am Karen, I sure am.” I said as I went to sit back.
“Mhm, what are you looking at?” She asked.
“Oh uh, just you.” I replied innocently.
“Yeah, right.” She replied as she stood up, bent over to reach something behind her laptop. Her breasts were almost completely visible.
I uttered “oh my god”, I thought I said it in my head.

She came back and leaned forward on the desk keeping her cleavage right in view. She smiled.
“What is it?” She asked playfully.
“N- nothing, uh, I’m a-all right.” I said shakingly enjoying every bit of visible skin.
“Are you really sure?” She asked and winked.
“Yeah yeah, just really warm.” I said as I noticed that I was running red.
“Just hot huh?” She said
“Yeah” I replied
“Well I have the same here. I’m so hot today phew.” She waved. “I am not sure if you noticed but I had to take off my bra because of it.” She added

I just looked and nodded.
“I mean I hope you don’t mind. Normally I take it off immediatly, but since we talk alot, you’re a co worker, you have a girlfriend, I didn’t want to embarrass you.” She sad. She sat back down and her breasts were jiggling.
I was focused on only getting her to lose her top. I so desperatly want to see her topless.

“Uhu” I uttered. As I was zoning out on her breasts I couldn’t hear much of what else she said.
I remembered her saying she was hot. So I decided to be bold. I couldn’t care for anything. I needed to see her.
“If you’re so hot, take off your top too.” I said.

A moment of silence followed. She looked at me. Bit her underlip as she put down her glass. She looked at me.
“Well then. Highly inappropriate.” She said.
I just looked.
“But it will be our secret.”

She rolled her chair back. I saw there were sweat stains on it. She looked at me, with a serious face. A light smile was visible and she winked.
Her hands went cross over each other and pulled her shirt up from the bottom. Her belly button was exposed first. Followed by an underboob, then two pink nipple. They were rather small and hard. She proceeded to go over her head and threw her top away.
She let her arms rest beside her body and she sat there topless.

Those were two beautiful, big breasts. Her slim body made it perfect.
She smiled. I was in awe.
The only thing that came out of my mouth was “fuck, I’m horny.”

I was horny indeed. I felt how my cock was getting harder at the sight of Karen sitting topless. I felt like I was in a dream.
“I’m sorry what?” She asked as she came closer and her breast jiggled on the movement.
“I’m horny now” I replied.
“Oh.” She said as she ran a bit red and was getting shy.
“How do you know?” She asked.
“Well Karen, I’m getting a huge erection at this minute. Staring at you.” I said.
“Am I that attractive?” She asked.
“You’re gorgeous. Stunning. So much woman.” I replied. “I like it.”

“Show me then.” She said.
“Show you what?” I asked caught off guard.
“Show me that boner, I want proof.” She said
I was hesitant at first. Should I go on with this? I mean a co worker is a professional relationship. Plus I have a relationship. But somehow my hormones won the battle against my conscience.

I stood up and the bulge was already visible in my pants.
“Oh my” she said.
I loosened my belt, unbottened and unzipped my jeans and let it drop down. I was there in my underpants, bulge even better visible.
‘Sorry honey’ I thought to myself as I slowly put off my underpants.

My hard, veiny cock was visible. Girthy, quite lengthy, throbbing. It bends downwards when it’s hard, so it’s a bit curving. A big tip that was exposed. My balls were hanging down because of the heath.

I saw Karen’s mouth drop. She leaned back.
“Oh my god. That’s huge.” She said. “You weren’t lying.” She added
“Told you.” I said.
“Such a beautiful cock. My god. I’m jealous of your girlfriend.” She said
“Why?” I asked.
“I mean if that’s the dick I had, I would suck and fuck it every day.” She replied whilst olaying softly with her nipples.
“How long has it been since you came?” She asked.
“Couple of weeks.” I said.

She stood up and took me to her sofa. She put her laptop on it and went away.
When she came back I saw she only wore underwear herself and she brought sex toys. A dildo of quite a large size.
“Look. I don’t do this. But honestly, jerk off and cum for me. I would love to help you with that. It’s a shame you don’t get that much sex.” She said as she was taking off her underwear.

She sat in front of of the pc, legs open exposing a pussy. She had a small bush on her bladder, but everything else was clean shaven.

She took a vibrator first and put it on her clit. She started moaning as her breasts were moving up and down on the rythm of her moaning. “Jerk off for me.” She said.
I sat down in the same position on the sofa so my balls were exposed.
“Mmmh fuck, this feels nice. I wish it was your tongue down there.” She moaned as the vibrator kept teasing her clit.
“I would love that too. I also would have loved for you to suck my cock here actually.”
“Mmh I bet you would, and I would do it with pleasure.” She moaned.

I massaged my balls as I was jerking off slowly, enjoying every minute. I wanted to cum so much for her.

She took her dildo and sucked it first to get it wet. “I’m thinking of you when I put this inside of me now.”
She brought the dildo up to her vagina and slowly put it in. I saw how it lightly stretched her. Her head was hanging back with pleasure.
“Ooooh fffuuuck I wish it was your cock darling” she moaned.
I moaned back “so fucking jealous of that dildo.”

I felt after 20 minutes of holding back I couldn’t hold it. “Karen, I think I’m about to cum.” I moaned.
I jerked and my foreskin was going over my tip, which by now wash shining with precum. A bit of it was on my balls.

“Oh yes, you are? Please, don’t hold back. Squirt it all out baby.” She moaned as she was going hard inside her with the dildo. I saw how a wet sport was forming on her sofa. The sound of the dildo entering her wet pussy was beautiful.
“Oh I’m cumming, oh fuck, oh yes, oh fuuuuck.” I moaned.

I squirted big loads of sperm. It squirted ik the air, it went on my body, a bit came on the sofa, some of it ended on the pc. I kept squirting cum, pumping it all out.

I stopped and looked around. Everywhere was cum, but most of it was on me.

“Oh my god. That was so much.” She said as she let the dildo slip out and looked. “I wish it was all on or inside of me.” She added.
I was still recovering from the intense cumming.
“That was needed.” I said whilst out of breath.
“Indeed it was” she said as she was also out of breath. She sat down on her sofa.

I grabbed a tissue and returned to the pc. Cleaning it all up. She was holding her wine glass, sitting with her legs on top of each other. She smiled as I entered the camera. By now my cock had gone soft.

“So, this is not gonna form any problem?” I asked.
She shook her head.
“Sure?” I said.
“Very, it will be our secret. Don’t you worry.” She replied. “I enjoyed it.” She added.
“Me too. You’re a very sexy woman Karen.” I said.
“You’re really hot yourself.” She said smilingly.
“But we’re gonna have to cut the conversation. I’m gonna make some dinner.” She said as she got up and showed her breasts.
“Take a good look at them.” She added.
I did. I showed her my cock again and my body.
“I’ll be dreaming of it tonight.” She said.

We said our goodbyes and logged off.
I was torn in my moralities but strangley satisfied. I was lost ik thought as I saw a Whatsapp-text from Karen.
It was her in front of a mirror, fully naked. Dildo in one hand.
Caption read “thanks for the amazing evening champ.”

I jerked off to that image.

As I’m slowly entering my 30’s, having a child, moving out, I have been having many nostalgic feelings. Last 10-15 years were so intense come to think of it. All of the sad moments, happy moments, break-ups, finding love, losing and gaining friendships. I wouldn’t be here without all that, writing stories for you all.

But today’s story is a true story. Because it actually happened to me. Don’t expect any dramatic. Just the truth, how I lived it.

When I was younger I had a way with the ladies. At parties I used to wrap them around my fingers. Online I talked, sexted and sent nudes (consentually) to numerous girls.

This story however is about one of my ex’s who actually improved my sexual capabilities and sexual fantasies. Even helped fullfill some of them.

She’s one of those girls (or ex’s to generalize it a bit) that you know is bad for you but given the chance you would. She’s clearly such a case.
We’ll call her Chiara to save her anonymity.
At the time we had a relationship she had long and very blonde natural hair, wore pretty make up, had full lips, and she was a bit bigger. Not fat, but thick. Those hips did not lie indeed.
She had beautifully big breasts with what one can call pancake nipples, a small belly, a very big ass, and everything kinda jiggled.

She always had this fashion-taste of showing off her curves. Always had a deep cleavage, sometimes did not wear a bra, thight tops, and if it were dresses they were very short.

So what will follow here are three small stories of my most memorable sexual happenings with her.
Hope you enjoy, and Chiara, if you read this: thanks for the wonderful years.

First anal fuck

The first story that I will share here is how I came to love anal sex.

I went to her house, it was a warm june day, just right after the exams finished. Her exams ended a day earlier than mine, so we met up directly after I was done. We were home alone and well we did what any young couple would do when they have the house to themselves.

After we finished the first round we washed up quickly and sat in the garden to enjoy the sun. She regularly sunbathed topless and as I was reading something I loon at her and her amazingly beautiful and big tits were shining in the sun. I looked up and saw her neighbour was also enjoying the view.

We laughed about it and she came to sit next to me. We gave a kiss and I grabbed one of her tits firmly. She loved that. We were chilling. She broke the silence with the following:
“Baby, we have been together for five months. We should actually do something special.”
I nodded. “You’re right, nice five months though.” I replied. “Well if you want to do something special you can try and give me a blowjob until I cum.” I jokingly added.
“Ha ha, funny.” She replied “no seriously, we should do something special actually.”
“What do you have in mind?” I asked curiously.

A moment of silence followed as she was thinking and took a sip of her cocktail. I grabbed my beer and emptied it.
“Do you want another one?” She asked
“Sure” I replied.

She stood up and as she stood up her tits jiggled as well as her beautiful big ass. She came back with a beer and just said:
“I want to try anal” as she smiled and handed me the beer.

I was caught off guard by her statement, but not in a bad way. I have been saying I have always been curious about anal, and she didn’t shy away from that idea either.
“Isn’t it gonna hurt?” I asked
“Honestly, I have lube here and I have neen secretly playing with my ass for a couple of weeks.” She confessed.

I went silent for a bit. Thinking. I wasn’t mad because she didn’t tell me, I was curious. I understood why she didn’t tell me immediatly.

“Say something” she said worryingly.
The only thing I said was “show me”.

She was relieved by that statement and we both put our drinks down. We got up and moved through the house up the stairs. In her room there was a closet and she opened one of the drawers. In there there was lube by Durex, what I saw as a dildo, another one of medium size and a butt plug.

I studied the objects as those were the first sex toys I ever saw in my life. As I grabbed the buttplug I felt it was iron and saw it was shiny. Short, compared to the bigger dildo-toys. Somehow the thought of it going inside of Chiara’s ass was arousing. I only wore underwear and I felt myself getting hard. A big bulge was quickly visible.

Chiara saw it and smiled, bit her underlip softly. “So what do you think? Should we try it?” She asked as she grabbed my bulge and gently carressed it.
I liked the feeling of her hand down there. And my curiosity only grew.

“I would love to try it” I said with a longing look at her body. She smiled, came in to kiss me. As we were kissing passionatly she undid herself from her red see-through thong. I undid my underwear and the tip was touching her body. She stroke it first to make sure it was hard. She went on her knees and slowly took my cock inside of her mouth. She looked up at me and I saw and felt how hard she was sucking it.

I moaned and occasionally pushed her head down on my cock so she made a chocking sound. I felt how a mix of spit and precum was dripping on my balls. I let my cock slide out and pushed her on the bed.
‘If she doesn’t enjoy it, at least I can do this’ as I start licking her pussy. It was wet already, but I did it for my pleasure. With every slow lick that ended with a touch at her clit she moaned. I let my eyes look up and saw how her breasts were moving up and down alongside with her moaned breathing. Her hands went through my hairs and sometimes the tension was so intense she actually held my head between her legs.

She stopped me and pulled me on top of her. “Fuck me like this first” she whispered. I inserted myself deep. She was laying on the end of the bed and let her head hang over the edge. I started slow, slowly progressing to actually fuck her. “Yes, yes, like that. Fuck me like a slut baby, fuck me” she moaned louder. I kissed her neck as I kept going. At the same time with every thrust you could her my balls clapping on her pussy.

I let myself slip out and turned her with her head down and ass up. Went back, grabbed her hips firmly and started fucking her from behind. “Mmmmh, fuck, mmmmmh” she moaned. We were both getting sweaty from the seemingly porn-ish fuck session. I looked beside her and I saw lubricant and the buttplug.

It first her little asshole was staring up at me. So as I was fucking her I slowly brought my thumb to it and penetrated her ass. She got up and I started to calmly fuck her as I was also focussing on me fingering her ass at the same time. She turned and had a loon of shock. “Omg” she said.
“Everything all right?” I asked worryingly.
“Mmmh, yes, that feels amazing” she said.
“This?” As I let my thumb slip out and inserted my middle finger, gradually deeper.

Her eyes went up and she went down with her head again on the bed “fuck, yes like that. That feels amazing”
I completely stopped and whilst my cock was still rockhard deep inside of her I only focussed on fingering her ass. Slowly I went in and out of it with my finger.

She was moaning. Enjoying every feeling and touch. She said “get out and put some lube in it and on your dick baby. I want to feel you there.”

So I did as she requested. I poured a good amount of lube on her ass, put some on my middle finger and inserted it a bit. Proceeded to cover my cock in it. It felt warm, slimy almost. As I was done with covering my rock hard dick I brought it closer to her asshole.

“You ready?” I asked nervously.
She sighed, I did not notice she was rubbing herself whilst I was preparing everything. “Yes, be carefull though”

I grabbed her hips with one hand and with the other hand I held my lubed-up cock. I was so hard my tip was exposed out of my foreskin and brought it up to her crack. I first went up and down a bit to get a feeling. As I was doing I felt her asshole passing by. I stopped at it and whilst holding my fat and hard cock I slowly started pushing myself in. It felt too thight at first. But then I saw she actually held an ass cheek to widen it, so it would be easier.
“Calmly baby” she whispered shakingly. Not sure if it was out of excitement or fear.

I pushed a bit harder and I didn’t get in. She just said “just push really hard” as I did what she said.

Without any doubt I saw and felt my tip disappear inside of her ass. As I got in I heard her going “OH FUCK” as she gasped for air. Her ass shook a bit with the feeling of my tip entering. The sensation was different than what I was used to. It felt strangly amazing, it felt exhilirating.
“Don’t stop baby.” She said “deeper” she moaned shakingly. I carefully proceeded to push deeper. As I went deeper she came up to lean on her hands as she was in doggy position. She turned around, her face was red. She was sweating and had a moaning face. I made eye-contact with her and with every cm of my cock inside her she moaned louder. “Oh my fucking God.” She moaned “That feels so good”

“It’s really really thight” I moaned as I felt her ass around my cock. I looked down and I saw I was quite deep. So I grabbed her hip and slowly started fucking her. Slowly, really slow. Every stroke was immensly good. It was so thight, I saw how her head was arching backwards. With every slow thrust she got more and more used to it.

It a certain point she turned her face around and simply said “fuck me harder babe.”

So I did. I went quicker. Thrusting deeper, let the entire length of my cock beside my tip slide out, only to push it deeper. I went so fast her cheeks were clapping. But it was barely hearable. Chiara was screaming. Not from pain but pleasure.
“HARDER, FUCK ME HARDER, FUCK ME BABY” she screamed.
As we continued I felt I couldn’t hold it that much longer. “I WANT THAT INSIDE OF ME” she screamed. Indicating she wanted my cum in her ass.
For her pleasure I started rubbing her clit. The extra sensation on top of getting fucked in the ass was sometimes so much she laid her head down.

I felt myself climaxing. “Fuck, fuxk” I moaned loudly as I released all of my cum deep in her. I let my hand grab her hips, which was extra wet from her pussy. As I was throbbing my cock inside her she moaned “oh fuck baby, oh my god, that’s so much cum” as she arched her back and laughed moaningly.

I let my cock slip out of her thight ass. It was followed with a huge load of sperm dripping out of her ass. She immediatly fell down on the bed with her legs shaking. I layed down on the bed next to her. We kissed and smiled. “That, was fucking good” I said.

She kissed me. “I still feel your cum inside and dripping” she said.
“Well, it was alot.” i replied.
“Just how I love it” she said as she gently grabbed my balls and leaned in to kiss me.

We were kissing in the hot afternoon-sun, all sweaty.

And that’s the end to my first anal. It’s still memorable to me. Tell me what you thought of this one!
Next one following soon!

Ws