tagAnalAnal Sex With Older Men Ch. 01

Anal Sex With Older Men Ch. 01


I was 22 when I first had anal sex. I was having an affair with a married man, Henry, who was a builder. He was maybe 35. I would see him a couple of days a week after he'd finished work. He'd call and I'd meet him in a quiet street close to my parents' place, where I was living after divorcing my husband. We'd drive somewhere (a building site, usually) and make out in his truck. It was a big yellow ute with a bench seat wide enough to seat 3 people. If he was in a hurry I would just give him a blow job. But if he had more time, I'd lie along that wide vinyl seat and we'd make love.

I loved sex with Henry. He was a big macho guy who always knew what he wanted. I loved his sweaty smell, his broad chest, thick hairy forearms. And I loved his cock. It was long and thick and had a smell and texture I just loved.

I thought he was the world's greatest lover. He didn't say much but just his hand on my face or neck would make me melt inside; or the look of pleasure in his brown eyes as I kissed him would make me want to do anything to please him. And sex with Henry was no two minute flash. I was already used to giving lots of oral sex, but not with a cock that big. That year I built up pretty strong jaw muscles from all the blow jobs I gave him. He never came in less than 15 minutes, and sometimes I would suck him for far longer. I also learnt how to control the gag reflex.

He would always come in my mouth. The first time I gave him a blow job, he clamped his hand on the back of my head and growled at me to take it. I always loved the way the underside of his dick would pulse and then the warm jizz would splash into the back of my mouth. He expected me to swallow it all, so I did.

But best of all, I liked it when we fucked. Just the way he would push me back along the seat and feel under my skirt, eyes full of lust, would make me wet. Sometimes he would suck my breasts for a minute or two, but mostly he would quickly have his shorts or jeans off and, hard cock in hand, get between my open thighs. Sometimes I would cum just from the way his fat dick stretched my little cunny as he entered, pushing and heaving to get all the way in. And then he'd thrust and thrust, his heavy body crushing mine, his thick pubic ridge flattening my labia and clitty, each time he thudded forward.

Before Henry, I'd rarely had an orgasm from penis-vagina sex. Either it simply didn't stimulate me or didn't go on long enough. But with Henry's big cock stretching and pounding my pussy and the sheer physicality of sex with this alpha male – well, I can't think of a time when I didn't come at least once.

Afterwards as we sat smoking and he drove me somewhere close to home, I could feel my vagina all battered and pulpy and satiated. Back home I would change my panties, smelling the thick mixture of juices that had soaked the gusset, often tasting it and thinking of the next time I'd be with him.

Then one afternoon as we sat in his truck after sex, he told me that his wife Rhonda was taking their 12 year old son and going to stay with her folks for three days – all the time she could get off work at the supermarket. Her parents lived out in the country and there was some crisis with her father's health. Henry said he would pick me up the next day as per usual and we could go straight to his place.

I was real thrilled and had all these plans to cook and look after him. But when we got to his place, he just wanted me to heat up the food his wife had left for him, then sit watching TV and drink beers. By the time we went to bed, I was pretty tanked. I'd had some expectation about a kind of romantic honeymoon thing, but Henry was all matter of fact. He just stripped down and went to the bathroom. When he came back in he didn't seem to notice my sexy lingerie, just lay down on the bed and pulled me to him.

Well I was just happy to be with him making love in a nice double bed, no chance of being interrupted or him having to rush off afterwards. Maybe it was the alcohol, but I didn't cum for a long time. Henry then urged me up onto hands and knees, fucking me like this for the first time. Sure I'd done it doggy style with other guys, but not with Henry in his truck. Now Henry's big cock was touching places that made me feel damn good.

I was getting into it when Henry slowed down and told me to reach across to Rhonda's bedside table, open the drawer and take out the jar of Vaseline. I kinda knew what he was going to do and it was confirmed a couple of seconds later when he greased up my anus. 'First time?' he asked as he pushed a big finger at the centre of my unyielding ring. I nodded, lower lip between my teeth. He told me to relax and after a moment I was able to enough so that his greased finger slipped inside me.

I decided it wasn't so bad as he worked it around and back and forth. But I got real apprehensive when he put his big cock head against the little hole. It took a lot of coaxing to get me to relax enough, and the initial stretching was bordering on painful. But once he was in, I adjusted real quick and was relieved to find that I could take him this way. For a while I felt like I needed urgently to go to the toilet, but that gradually faded as Henry's cock stroked in and out. He hissed that I was real tight and that he had to be careful not to cum real quick.

As he thrust steadily into my rectum I wondered how often he had anal sex with his wife, imagining Rhonda up on her hands and knees, her heavy tits and big belly wobbling, whining voice complaining (or so I liked to imagine) as her hubby sought release. I wanted to think that even though it was my first time this way, I could give him a better ride. I started to hump back and Henry panted that I was a natural. I was proud and kept meeting his thrusts till he strained and came.

Afterwards we went quickly to sleep. But I woke in the middle of the night and stayed wide awake. The bed smelt of Rhonda's cheap perfume, my side sagged – no doubt from all the years of having a 100 kg woman sleeping there – and in the dim light I could make out the family pictures on the wall and on the dresser. I felt really uncomfortable and couldn't wait for morning.

That was the beginning of the end for me and Henry. It was over in a couple of weeks. I couldn't seem to make him understand what was wrong and it was clear that he had no intention of changing any of his arrangements. But I sure did miss the great sex and it was 8 months before I had another bf.

And it was a couple of years before I had anal sex again... But that, as they say, is another story.

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