[FM] Losing my anal virginity to the sexy older man I met on Reddit

On the outside I’ve always been a good girl. I was too shy to flirt with guys and too nervous about getting physical. Reddit and Kik really brought me out of my shell – at the age of 24 I discovered the Kik subreddits and soon I was sexting and swapping dirty videos daily. I got my confidence up, and finally hooked up with some guys I met on Tinder. Those guys were never enough though and I still loved getting dirty with my guys on Kik. I had a bunch of “regulars” and was connecting with new guys on a regular basis.

Then I connected with someone local. He was 40, already a silver fox, with a thick groomed beard. He was tall, barrel chested, and gloriously hairy. At first I played things coy and shy. I have a girlish face, soft brown eyes and hair, and always wear glasses. I’m average height and on the plump side (and rather busty).

He seemed to find me so sweet and cute… but I couldn’t help myself – he was exactly the type of older man I always felt so attracted to. We had fun goofing around and being silly, but I wanted to see how dirty he was. And fuck, once I did, I was lusting after him. We had talked about how I didn’t feel confident giving blow jobs or riding dick, and how badly I wanted to try anal. He had an extensive sexual history and promised to show me the ropes. He didn’t have to work too hard to convince me to meet up with him.

The first time we hooked up was awesome – but I want to talk about the second time, when he finally fucked my ass.

*** Sex stuff begins here! ***

On a Thursday night, while my roommate was away at her only evening class of the week, I let him into my apartment and we quickly crawled into bed together. We put The Office on but quickly ignored it to make out and feel eachother up. I was wearing a pink tank top and bra, and black work out shorts. He wasted no time, rubbing my pussy through my shorts while he kissed me. I was already so wet, he could probably tell. He slide his hands into my shorts, and told me I was a good girl – I hadn’t put any panties on, just like he’d suggested. He began rubbing my clit and teasing me. I was moaning and thrusting slightly against his hand. Finally he slid his fingers into my pussy, commenting on how his fingers were already coated in my juices. The shorts were getting in the way, so he told me to “take off those fucking shorts” and I of course obliged! With my pussy full exposed, he wasted no time, absolutely finger blasting my pussy. At this point we were both still wearing way too many clothes. We took a moment to undress, and then he told me to suck his cock. I crawled between his legs and went to town. He encouraged me to let it get as wet and sloppy as I could. I bobbed up and down his cock – following my lips with my hand, slurping and sucking as best I could, gagging fairly often but loving how his cock felt in my mouth. He held my head down on his cock as long as he could until I was gagging and coming up for air. He mustn’t have minded my amateur technique because he said, “Fuck, I thought you said you weren’t good at this?!” Then he told me to get up and ride his cock. It wasn’t until he reached around behind me to play with my pussy that he realized I had a butt plug in. It was just a small one – but it sure got me turned on and helped loosen me up back there. I rode his cock for a bit but he quickly told me, “Fuck, I can’t stop thinking about that plug in your ass right now.” So I asked him if he wanted to try anal. He told me he was game if I was!

I popped my plug out, then we got out the bottle of lube and I slicked his cock up for him. Then he stood at the side of my bed and I got on my hands and knees, and scooted up to the edge of the bed. He lubed up his fingers and inserted one into my asshole. He asked me if I liked it and I encouraged him to keep going. He worked in a second finger, making sure to get my asshole slick with lube. It took us a moment to adjust our position so that my ass was at the right height and he slowly began working his cock into my asshole. There was a slight burning stretching feeling but I was so fucking turned on and excited. When he asked if I was okay I said, “Yes, keep going!” He worked himself in and started thrusting slowly. I literally could not stop myself from moaning like a ridiculous pornstar, but fuck it felt amazing. He picked up more speed and was soon fucking me hard. I was arching my back and moaning uncontrollably – the pleasure was out of this world. He grabbed my shoulders and pulled me backward, then reached his arm in front of me and grabbed my throat. Thrusting into me hard and fast, holding me by the throat. I was practically cumming from the pleasure. We couldn’t keep this pace up forever – he slowed down, I splayed out onto the bed. He pulled out and suggested we go wash up. We walked into the bathroom and I grabbed us towels and got the shower going. As the water was warming up, he grabbed me and pushed me up against the wall, with me standing with my legs on either side of the toilet. He slipped his cock into my asshole (much more easily this time) and fucked me briefly. He pulled out and have my ass a little smack and we got into the shower. We lathered eachother up and I washed his cock nice and clean. Then he pushed down on my shoulder, so I sank to my knees and sucked his cock for him, him thrusting into my mouth and holding the back of my head. After a bit he pulled me back up again and we shut the shower off and toweled ourselves off. Back in the bedroom, he still hadn’t finished himself off.

He asked if I wanted to try a new position, and had me lay down on the bed, with my stomach on the bed. He straddled my legs and entered my pussy from behind. Then he had me twist around, slightly onto my side so I could look back at him over my shoulder. From that position he could pull back on my shoulder, wrap his hand around my throat, and give me some nice sharp slaps on the ass as he fucked me. He was fucking me so deeply that I finally came on his cock, moaning like a slut. Then he put his hand against my back and pushed me down into the mattress. He fucked me into the bed and pumped me full of his cum.

Afterwards we cleaned ourselves up again and then cuddled in bed. He showed me some stupid videos on YouTube… Soon he made his exit before my roommate arrived home to discover this older guy in our apartment.

We would have kept fucking eachother regularly but it turned out that when he said he was separated from his wife, he was actually still living with her and going to attend marriage counseling with her. So I decided to cut things off before we could get ourselves into a bad situation. But damn, do I miss how that man could fuck!

I haven’t had anal since then but I know I will sometime down the road. :)

Source: reddit.com/r/gonewildstories/comments/bz7i20/fm_losing_my_anal_virginity_to_the_sexy_older_man