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I had been seeing a man older than me for quite some time when this first happened, don’t get me wrong I had fucked boys my age but a man just a bit older than me was so much more fun and he really knew how to show me a good time.
Ok, so this man was 20 years older than me, which may seem like quite a stretch but we were just suited to one another. He was married but no longer with his wife, instead of going through the divorce process they just decided to stay married and friendly with one another. He was totally honest with me from the moment we met inside an upmarket bar in the center of the city.
We talked for ages sitting on the high bar stools and straining to hear one another over the music. As the night went on we decided to head back to his apartment, it was a bright apartment with an amazing open plan design. He had the most magnificent oak bed with beautiful white bedsheets, we talked over a glass of red wine and then he stripped my clothes off and took me into the bedroom.
The First Time We Had Sex
I straddled him completely naked and unzipped his trousers, he was in total ecstasy watching my body. He told me that he hadn’t seen a body quite like mine. He grabbed at my small pert breasts and slid his hands over my body as I pushed his cock inside of me. I was really wet and my tight pussy took his whole cock which made him groan with pleasure. I bounced up and down on his hard cock and kept my hands firmly on his chest as I did so.
We both moaned, sweat running from our bodies, grabbing at one another. I put in my best work bouncing up and down as hard as I could and guiding his hands to my breasts and making him pull my hair. My body was building to orgasm, with each thrust lightning bolts jolted through my clit and I told him just that. I knew I was going to cum and when I told him this he grinned. I kept on bouncing until I felt an eruption from within me and all of my pussy juices made their way down his cock and I was left breathless. My cumming drove him wild as he grabbed hold of me and thrust so fast and hard that It wasn’t long before he came and we fell asleep in each other’s arms.
The Morning After
I woke up the next morning in a hungover daze, the bed was empty and I was still totally naked. There were no curtains on the windows, they looked onto the huge city skyline and I could see busy people making their way into work, which is where I should have been heading.
I picked up my things from the floor and dressed quickly, knowing I had to get home and change before I set off to get to work on time.
As I was fastening the button on my jeans in waked the handsome older man from last night. He smiled at me and then made me a coffee, we exchanged awkward pleasantries and I dashed out of his apartment, back to mine and then finally headed to work.
I worked the whole week and this man kept popping into my head, cumming on his cock was thrilling, the way he made me feel was beautiful and he was a total stallion in the bedroom. I kept hoping I would bump into him but I didn’t want to just knock on his door and I had been so busy at work. That Friday I decided to head to the same bar I met him in, to see if I could bump into him again. I went with some girlfriends just in case he didn’t turn up but I was in luck. He was sat at the bar when I first walked in and he grinned from ear to ear when he saw me.
I was wearing a tight red dress and heels a bit different from my jeans and t-shirt that I wore the first time that we met.
I immediately went up to him and kissed him on both cheeks, he bought me a drink and we started talking. However, it wasn’t as innocent as that, he kept on touching my leg and we would smile at one another in a way that meant ‘I am so horny‘.
It’s no surprise that we once again ended up at his place and fucked like newlyweds. He fucked me in all sorts of positions and even licked the cream from my pink nipples.
The next morning was a Saturday so we stayed in bed and made our way to breakfast after snoozing and basking in the morning sun that shone through his windows and that’s how our relationship started really, most evenings we would spend time together and making each other cum.
I loved the way he treated me, he was the best cook and always had the most amazing wine at the ready for when I finished work. Sitting in his giant bathtub, soaking in the lavender-scented water was delicious and it was even better when he would hop in with me and we would fuck in the bath.
The things we did were incredibly sexy and it wasn’t long before we both wanted to start experimenting with more things, things like sex toys (he introduced me to this dildo, it’s amazing), roleplay, different more experimental sex positions, and just about everything else but the one thing that I had never done is anal sex.
Men had fingered my ass, slapped my ass, and even licked my ass but at this point, my ass was a total anal sex virgin.
My First Time Having Anal Sex đź’—
One night whilst drinking a glass of wine, we had his log fire burning and we were curled up naked under a blanket whilst watching a movie. We began touching one another under the blanket and he slipped his fingers inside of me whilst I caressed his penis with my hand.
The kissing was so sensual and we were both breathing deeply and suppressing our moans.
He gently slid a finger into my ass and it felt amazing, I moaned in total ecstasy and I bit my lip. His cock was bulging from under the blanket and when he was inside my ass I could feel him becoming even more turned on.
We made our way to the carpeted floor in front of the log fire and he went down on me, the act was so sensual and our bodies were so warm. His tongue swirled around my clit and my young body was a stark contrast to his aging skin.
I was on the edge of orgasm as he played with my pussy and dipped his finger into my ass, I was in total submission and he was totally bewitched by me.
He asked me to get onto all fours and I did and he gently slid his cock over my ass opening and I told him to push it inside of me. We had our favorite lube nearby which he used as he guided his throbbing cock into my tight ass.
He had told me before in conversation that his ‘ex-wife’ had never wanted to have anal sex so it was something that he was new to as well.
As I stayed on all fours I could feel the pressure as it built up around my ass, my pink pussy was throbbing and soaking wet but my ass wanted it as well. He kept on gently pushing himself inside of me and with the anal lube working its magic and the weeks of preparing my ass and his gentle nature he eventually glided his penis inside of my ass. It was a sensational feeling and we both groaned in pleasure. He gently thrust back and forth, pushing his head back as he did so. I wanted him to go faster and faster and began bouncing back on his cock.
It felt so much tighter but it was like being a virgin again, he told me he couldn’t control himself that he had to cum, I told him that he couldn’t, that he had to wait. I kept on thrusting whilst he gripped my waist and grabbed at my ass.
He was desperately trying not to cum so I didn’t let him suffer for too long, I let him cum inside my ass and the warm oozing liquid filled my ass and dripped down my leg. He bent over me panting and gently removed himself from me.
It was an amazing feeling and fueled a passion in us both, anal sex was our new favorite thing to do. It felt great for us both and there was so much fun to be had. Some of my favorites were when he would fuck me in my ass and then thrust a realistic dildo into my pussy so that it felt like I was fucking two men, this is also a fantasy that I still want to fulfill to this day.
I loved every experience I had with that man, it was unfortunate as he got back with his wife but I am sure he looks back at our time together with glee and the old bastard must still masturbate thinking about my tight young body.
Thanks for reading my story on my first anal experience, if you have any other stories you want to hear about just let me know in the comments area below.
Jess xoxo
Update: If you want real erotic pictures and stories with full nudity and real couples talking about their naughtiest sexual experiences sign up to my membership.
Lucy
I’m going through a stage where I’m loving anal sex, never thought I’d ever say that. Once I got my head round trying it and relaxing, it felt amazing and it drives my boyfriend wild <3
BitchTopia
wow, I am so pleased for you Lucy. I know exactly what you mean about never thinking you would enjoy it, I am so glad that you love it. It’s really fun to try new things from time to time. Thank you so much for your comment, love, Jess xoxo
Paul
I’d love cum up your tight asshole
Edward Thompson Jr
My ex wife loved up the ass. Not at first when I flipped her over onto her stomach and took her hard. After that she wanted it all the time and for me to cum in her ass. It was such a turn on for her. The same with my currant wife. When I fuck her in her ass she cums so hard and so much. And both wanted to be on all fours or laying flat on bed and for me to take them hard after I got them lubed and stretched out. Then I was to pound and grind their ass. Was such a turn on for me especially when they would put a toy in their pussy while I fucked their ass
Joe
The reason is that your ass and cunt are separated by a thin piece of skin. Reality is that it is just as sensitive as the pussy. I dated a girl and thought I would never talk her into it. After I eased it in with in seconds she was banging my cock like it was the best thing she ever had. In fact her orgasms were so strong She squirted down her legs. Afterward she found some cum that had dripped on the bed and lapped it up. I also noticed after that she was good for trying anything. She would literally have a squirting orgasm when I shot my load down her throat. Needless to say she was worth keeping.
yum
yumyy
Sheryl
That’s a wonderful story!
I love anal! I get wet just thinking about it!
Boogie
My ex gave me anal as an anniversary present one year it was so tight and awesome that she said she felt like a virgin but we only did that on special occasions
DirtyAngel
The hubby and I are going for anal for the first time this weekend. I can’t wait to feel him inside me! Just thinking about it sends shockwaves to my clit!
KANESGIRL
Was worried about having anal for the first time, but love it now. An understanding and patient partner is always good. Started “suggesting” with a finger and when I didn’t complain he inserted a finger with plenty of lube used. Felt amazing when I relaxed into it and came very quickly. First “proper” time he was very patient, but decided to use a vibrator on my clit at the same time, so that was mind-blowing. NEVER once does he want to have anal sex if I don’t want to, and it’s 50/50 as to who says “shall we” tonight? Trying a dildo in my pussy at the same time or a vibrator on my clit is incredible and a dildo gives you the sense of two men. Luckily he doesn’t want a threesome properly so we use that as our “third person”.
Edd
We tried anal twice I loved it I’m not so sure about the other half I’d love keep trying but my cock is big and her ass is small.
TM
My wife and I were newlyweds. I had been wanting anal for some time and she had no idea of what I was planning. We were having sex, it was a very warm evening, and I asked if I could enter her. She said yes but slowly. I couldn’t wait to get in her ass. It didn’t take long for me to unleash my load and as I did, she said, “I can feel you coming!” I love anal.
Later years… we’re in our jetted tub and I start teasing her ass with my toe.. she said, ‘If you want more, you just have to say so..”, I jumped out of the tub and and readied the lube, went down on her and she had a great orgasm, then I gently entered her pussy from behind. This was the best part and even after the years have past, I still get hard from her saying… “you know what you want, just take it”. How many lucky husbands have wives that say that. I slowly entered her a bit at a time, and then she said.. “further.. futher..” I was all in, came.. and cannot tell you what a great night that was. Mesmerizing, Phenomenal, Absolutely effing great – haven’t had it since. She has constipation after and won’t let me ‘in’ that area anymore. I sometimes think I’ll have an affair just to have some ass but still hoping she’ll allow us to have those ‘special times’ again. I like anal but pussy is still the best.
See my Email
i love you anal stories but I think anal is so much better if the poop factor is solved by cleaning her out before hand , followed by a shower together.
SuperD
Jess I love your blog and will definitely becoming a member for sure it’s a huge turn on reading your blog which I just came across . I can’t get enough of your blog thank you
BitchTopia
Thank you so much for your kind words <3 <3
Mandy johnson
Super sexy story!!
I am going through an anal stage, bought a dildo specifically for it and omg! I can’t stop.
Jhon
Spent 6 months with 24 year old young woman who ask me to take her ass and fill it with my cum.. well she said just do it without anything, who also! It felt great sliding into her , tighter than a pussy and very enjoyable , lasteded couple minutes then filled her ass to moans of joy, . We stayed together for a few more months and she always wanted her ass filled, she love it more than straight sex , I must say I enjoyed many great climaxes in her tight ass. After we parted I had every lady in the rear with great enjoyment on my part, they never said if they enjoyed or not
Jaysen
Am from Hindu caste and love to have sex. I never had anal sex till recently my wife allowed me. Before that happen, she used to let me finger her ass during sex and that was amazing feeling for both of us but recently she allowed me to put my dick and she is also loving that.
By the way, my wife got a fucking nice body everyone would desire. One day we went for vacation in Thailand and she was wearing provoking things in all her outfits and you could see how people wanted her.
Nowadays we are always into anal sex and she loves that.