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First Time With Mature Older Woman

"Tommy discovers the beauty of sex with an older woman."

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Hello, Lush friends!

After more than five years of reading, I finally decided to share something of my own. It starts like this:

The story I’m about to tell is partly true, and it happened to me about twenty years ago, back when I was still a young tiger.

My name is Tommy, and I was 23 at the time. I worked as a warehouse assistant in the auto-parts department of a large company. Most of my coworkers were men, but there were also three or four women. One of them was Tanya. Tall, slim, blonde, forty years old, divorced, with three kids behind her. Two of her children were grown, and only her youngest son, Mikey, still lived with her.

She was a delivery driver for the company, and quite a few of the guys joked around with her and threw sexual comments her way. But, as I found out later, she hadn’t responded to any of them. Maybe they were too crude, or maybe she was looking for something different. I often helped her gather deliveries for her route, and when she came back, I was usually there to help again. After all, she was a woman, and sometimes she came back with brake discs and pads that weren’t exactly the kind of thing a lady should be expected to haul around. Over time, we started sharing more and more with each other and became close.

August was coming to an end, and I asked her if she had any plans to go to the seaside, since summer was clearly on its way out.

“Oh, Tommy, I don’t know. The little one is still on summer vacation, but if something comes up, I’ll send him to his grandmother and take off.”

A few days passed, and she told me that a gentleman who had been hitting on her had arranged a house for her to stay in for a few days and relax. Her eyes lit up as she said, “They transfer our money around noon on Friday. Want to come with me on Saturday?”

“Well, sure. I’ll take a few days off too,” I replied without even thinking twice.

At the time I was fucking a twenty-eight-year-old woman who was quite a wild one, but she had a lot of personal problems, so I never got too deeply involved with her. A curly-haired redhead named Katya. I couldn’t bring her home, so every week we fucked in a cheap roadside motel. Sometimes I stopped by her place and we talked for hours; she was already making plans for our future. I was there to kill some time and get a blowjob at the end of the night. Every time she blew me and then swallowed my cum. Sometimes I got her off with my fingers. When we were at the motels, she liked to have some white wine, and after that she had absolutely no inhibitions. She let me fuck her ass. All in all, she was a dream slut, but I didn’t feel emotionally close to her.

Tanya, on the other hand, was a completely different woman. I quickly cooked up a story for Katya that I was going to the seaside with some friends. She sulked a little, but I promised I’d call her regularly, and even though she wasn’t thrilled about it, she let me go. On our last night together, she emptied my balls nicely and told me, “I know that when you’re with the boys you don’t think much, but please be careful!”

To me, that meant: I know you’re going to fuck someone else, but at least wear a condom.

The night before leaving for the seaside with Tanya, I thought about her a lot and masturbated.

Saturday morning, she was waiting for me at the central bus station. We got into her car and took off for the coast.

Tanya was wearing a nice floral pair of leggings and a short tank top. She wasn’t wearing a bra, and when we set off, the cold blast from the air conditioner made her nipples hard and prominent. A few times I caught myself staring at her tits and adjusting my cock inside my shorts. The sly old fox just smiled and pretended not to know why I had a slight hard-on.

After three hours of talking, laughing, and flirting, we arrived and settled into the two-story villa. The first floor had been rented for the whole summer, while Tanya’s admirer had given her the second floor, which consisted of two rooms connected by a large balcony. A table with four chairs practically invited us to watch the sunset with a few drinks.

“So what did you promise the poor guy to get him to give you this floor?”

She came closer and whispered, “Maybe two or three times I accidentally rubbed my ass against him when I was delivering parts to him.”

She was incredibly direct and didn’t beat around the bush. I liked that about her.

I went into my room and waited for her to get ready for a walk down to the beach and something to eat. About ten minutes later, she was ready.

Wow. Tanya was wearing a short black dress and high heels, and now she was exactly as tall as me — 185 cm. I couldn’t help imagining what it would be like to fuck her.

We walked along the seaside promenade, and I saw men turning their heads to look at her. She still wasn’t wearing a bra, and her playful tits bounced with every step. What a woman.

After the long walk, we sat down at a little restaurant, and Tanya knocked back several vodka-and-Cokes. I was drinking too, but I still had one eye on what I was doing. After that, we decided to head back to our little house and finish our drinks on the terrace.

On the way back, she asked me to put my arm around her from the right while we walked toward the house. With my hand resting on her waist, I slowly let it slide down toward her ass. I don’t know whether the alcohol gave me courage or not, but I started stroking her, moving my hand between her ass and her slim waist. By then I was getting seriously hard, but I still had to wait.

The last little shop near our house was almost closing, but I ran over and grabbed a bottle of vodka and a box of condoms. The saleswoman looked at me, scanned them, and handed them over with a smile.

When I got upstairs, Tanya shot me a look.

“Don’t even think about going to bed and leaving me alone on the terrace.”

She went outside, sat down in one of the chairs, and lit a cigarette. A little later I joined her with two glasses loaded with plenty of vodka and just enough juice for color.

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I sat beside her and we started chatting. First we talked about all our coworkers, and then I slowly steered the conversation toward sex. She told me how difficult it was working in an industry full of men, and how they never really saw her as a woman.

“In the end, Tommy, everything comes down to one thing — getting fucked. My grandmother used to tell me: ‘Daughter, whatever you put in your mouth and your pussy is what you’ll have left.’ I try to think things through before I act.”

We talked a little longer, and I went over to turn on some music on the TV. I poured more vodka and juice and sat back down beside her. I slipped my hand behind her neck and started massaging her. She relaxed and let out a soft moan.

Encouraged by that, I leaned over and gently kissed her on the lips. She kissed me back, and a moment later our tongues were tangled together. I felt her aroused breasts beneath my hands. I gently pulled down one strap of her dress and began kissing and licking one breast, tracing little figure eights with my tongue. I lowered my hand toward her slightly parted legs. Beneath the edge of her dress, I could feel the damp patch that had formed on her satin panties. She smiled, and by then I knew there was no going back.

We stayed there cuddled up, talking, both of us knowing the night was only just getting interesting.

“Tommy, are you sleeping with anyone?”

“Yeah. I’ve got a friend I have sex with. She pushes things too hard, but I keep pulling away. I just don’t feel it with her. She’s twenty-eight and she’ll want something serious, while I’m only just starting to figure myself out. But yeah, for sex, she works!”

Tanya looked at me mischievously and said, “I recently started fucking Jimmy, the dispatcher at work, but he’s falling in love with me too, and I’m not looking for anything serious. I love bold adventures, but honestly, after two marriages and three kids, all I need is some good hard fucking.”

I stroked her hair again and started kissing her.

“Tommy, will you excuse me for a minute?”

She stood up, leaned forward, and kissed me. The next moment she shifted closer and took off her panties.

“Be a good boy and open your mouth.”

I obeyed without hesitation.

“I’ll be back in a minute!”

With that, she stuffed her panties into my mouth and went into the room.

Ten minutes later, she had showered and the lights were out. I sat on the terrace smoking cigarettes and breathing in the scent of the underwear she had left me. After a while, she appeared again with another full glass of vodka.

I had moved my chair toward the garden. She leaned over, started kissing my neck, and slid her hands toward my crotch. I was unbelievably turned on. She slipped her hands under my shorts and started squeezing me.

“Come on. Let’s go into your room!”

I didn’t need a second invitation.

“Promise me this stays just between us.”

“Of course. Enough talking,” I said, and started pulling her closer.

She had changed into a short pajama set but wasn’t wearing any underwear. While I kissed her, I squeezed her ass. I slipped my hand beneath her nightshirt and started teasing her clit. Her eyes widened, and she grabbed my ass.

“I want to taste you now!”

I said it and pushed her onto my bed.

She lay on her back and spread her legs. She put a pillow beneath herself and looked at me. I gently kissed her between the legs and then moved to her clit. She tasted incredible. I never would have guessed she had given birth three times. Her skin was incredibly smooth and soft. Her pussy lips were long and full. I bit and sucked them.

“Fuck me, Tommy. I want it.”

I put a condom over my hard cock and started fucking her. The damn bed was making a hell of a noise, so we moved onto the floor and the carpet. She moaned while I covered her mouth with my hand. She bit me and moaned again. We were like animals.

We changed positions, and she climbed on top of me, straddling me. The moonlight lit up her face. Our legs tangled together as I started pounding into her again.

“Your little girlfriend has no idea what she’s missing...” Tanya said.

A few seconds later I couldn’t hold back any longer. While she was still on top, I pulled out, removed the condom, and she took me into her mouth. I came hard, and she kept going. I was so overwhelmed by the orgasm that my teeth practically went numb.

After a while we went outside and lit cigarettes on the balcony. We finished our drinks and went back into the room.

I started kissing and touching her again. I put her on all fours and began kissing her intimately from behind. After a while I saw her reach down with one hand and touch herself again. I stood behind her and tried to move closer. For a moment I almost went the wrong way, toward her ass, and she wasn’t ready for that. She reached back and guided me back where she wanted me.

I felt incredible taking her from behind. I spread her cheeks wide. Then I wet my thumb and teased her from behind. She started moaning louder and moving against me harder and harder.

“Faster, faster... Fuck me!” she urged me.

I went harder and faster. She kept moving against me, and within seconds I was right on the edge.

“Yesss, goddamn it!” she cried.

She came hard too. Her whole body shook, and she collapsed onto my bed. Beneath her, a large wet patch had formed. We were both exhausted and sticky.

I collapsed beside her. I was breathing heavily, and my cock was already starting to soften. She kissed me and got up, slightly dazed. Holding herself as she turned toward me, she said:

“Get some good rest. Tomorrow I want more!”

She winked at me.

I went to the bathroom to clean myself up and then lay down in my bed. I kept thinking about what an amazing seaside trip was waiting for me.

What else could possibly happen?

That night had definitely left some very pleasant memories for both of us.

Published 
Written by White5nake
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