My Halloween toyboy adventure with a [M]il[F] (24/45)

I had been reading this sub for a while, and even though I've done some things worth of being here, I never felt like posting them. I feel like I should say this though: all that's written here happened last Friday, the night before Halloween.

Also, sorry if this is too long, I'm going to write everything I remember, and it's the first time I write about a sexual experience.

No costume yet, but I was still excited about going out, the previous weekend I had managed to get some extremely strong weed, so I just wanted to go out and have fun. I was going out with some friends to meet some fellow redditor at a party, so we shared one joint and headed to the party. It was so strong that we got there pretty high, got a drink each, and started walking around and talking to people, the party was at a bar, not too dark, with loud music that still let you hear other people. There were about 30-40 people in "our group", mostly dressed up, so it seemed like it'd be a good night.

We started to walk around and say hello to people, with the high still peaking, so it was a bit hard to hold a proper conversation, and I really have no idea with hoy many people I spoke to, or about what. I do remember a very annoying girl that might have liked me (later confirmed by friends), that just wouldn't go away. To give some context, I'm actually a quite good looking guy, tall, and athletic (I would never describe myself this way, but this is anonymous and it's relevant to the story I think).

A bit later I was finally coming down, when I saw this older woman sitting at the bar. She had dark hair, a nice face with a beautiful smile, and seemed to be in good shape. She realised I was looking her way, and when our eyes met, she smiled back – so I decided to give it a go. She was with a younger girl, who was probably around my age (24); I grabbed another stool and sat in between them, introduced myself and started talking. Initially she tried to get me to flirt with the young girl, and kept telling her how nice I was, how hot I looked… which at the moment didn't seem out of place for some reason. But I always had this fantasy of having sex with an older woman, so I decided to go all in, and started flirting with her more directly. She quickly got it, and after a while she literally asked "why me", to which I said something like "I've been with plenty of girls my age, and I think I have a thing for older women" – basically going all in. And it worked.

Lets fast forward a bit, after 1 or 2 hours talking I had learnt that she was married and had one kid. I also said that I was quite high when we started talking, and asked her if she did any weed. To my surprise she actually had a glass pipe full of weed in her purse! She then asked, "are we really going to do this then?", I knew it was the moment that would determine the rest of my night, so after a quick thought I said "I think we are" – smiling at her, but then I added "although I can't really promise anything…", because even though it was a fantasy, I was a bit worried that her being quite older wouldn't actually turn me on that much.

The younger girl knew the bouncers on the club next door, got us in and left – I'm not sure what she was thinking, but whatever, I had other plans that night. Once inside, alone in a club full of people dancing, we headed to the far side, with her leading the way. I actually felt worried that it would be too strange for her, because she must have been like 15 years older than everyone there. Well, whatever. When we got there I turned her around and started making out, for the first time. I'm quite forward so as soon as that happened my hands were all over her, and I could tell that she was loving this. I turned her around, got very close to her back and kissed her neck, while still playing with her boobs (which were pretty big, I grabbed them with my hands and there was still a lot of boob left!) and rubbing her pussy over her pants. She was really into this, I could feel her getting very warm. We did it for at least 20 minutes, or more, I really have no idea.

She took the pipe from her purse, and we smoked in the club for a while, that woman didn't give a shit about anything apparently! The pipe made my next memories dizzy, at some point we got in a cab, we stopped for condoms, and got to her place. Once there we drank some water, and I took another joint I had, we smoked about half (which is actually a lot, with this weed) and I sat on the couch while she went to the restroom. I actually expected her to come back wearing something sexy like in so many movies, but she came back with the same clothes, I guess she actually had to use the restroom…

This started to get pretty good now, she started leading the way, I actually prefer being "used", and the whole fantasy about being an older woman's toyboy started to really get me excited. We were just making out, but she was already touching me a lot, then lifted my shirt and started playing with my nipples. Holy fuck was that amazing, younger girls have too much to learn on foreplay, this was glorious, and my dick was still trapped under my clothes. She took off my pants, and continued switching between nipples and neck while rubbing me, I was moaning a bit by now, but the weed made me feel totally fine with the situation, I just wanted her to do whatever she wanted, and she knew it.

When she finally took off my boxers and went for my cock I was actually really hard, so all my worries about not being aroused by her disappeared. The blowjob was as glorious as I was expecting, slow at first, playful, and amazing — plus the fact that I was having a really intense high.

I reached for her top to take her off, I wanted to see her big boobs. They were much bigger than I thought actually, without sagging too much either. I buried my face in them, loving the feeling of being completely surrounded, then pushed them out of the bra and made love to her nipples, I was completely out of myself, enjoying every bit of this with zero embarrassment or doubts, it was feeling amazing.

We went for the bed, took the rest of our clothes off and I got on top of her, missionary style, making out again. I actually didn't want to eat her, even though I love giving oral. You know another advantage of being with an older woman? She LOVES you, and knows that it doesn't happen often; and seriously, as a guy, there's nothing better than feeling this desired. It had never happened with younger girls to be honest, and I was absolutely loving it. So after making out, I just laid on my back to continue enjoying her blowjob skills. She kept on saying how hot I was, how amazing my body felt… It was the biggest ego boost of a long time!

After a while, she got a condom, put it on me, and then sat on top on me, starting to ride me. I was now a bit tired of so much playing and teasing, so I grabbed her by the hips and decided to show her what a young guy can do. It felt amazing hearing her scream while I was fucking her as hard as I could, although I would also slow down at times, to never let her get used to what I was doing.

I then told her to get on her on all fours, for some doggy. Her pussy was so wet that I could just slide it with no effort, and this part was one of the best. She was just repeating how good it felt every few seconds, and I was having the time of my life fucking her at different speeds, sometimes brutally, others softly… Then telling her in her ear how I owned her, she was just mine at this point, it was insane.

We went on for a long time, in many more positions (the weed probably helped here), and I was starting to get a bit tired, but cumming is hard when you're high, so I got her on doggy again, and focused on me this time. Started a slow rhythm, making me harder all the time, until it was pure pleasure, then kept going, increasing very slightly, until I could finally feel it getting closer. After that I started going deeper, and came probably way too loudly. But it was fucking amazing.

We relaxed for a while, but then she told me to lay on my back, to give me a massage (older ladies rock, seriously). This was super relaxing, while also very hot, feeling her pussy in my legs and her boobs on my back. But then she got very close to my face, whispering kinky things, and telling me that she would have a lot of fun with me that night. I started moaning, fuck, I love being used. I think I actually told her.

She started to lick my ear, one gf had once started, but it felt weird and never did it again. This was another story. I was actually receiving pleasure from her licking my ear, all over my ear. It made me extremely horny, I just wanted her to do fucking anything to me by now.

I'm also getting a bit tired of writing, that was a lot in one go. If people like this I'll continue it, there was some interesting stuff after :) I know this is a long shot, but if you happen to be an older woman (35+) and are in or near NY get in touch! haha

Source: reddit.com/r/gonewildstories/comments/3rbfh0/my_halloween_toyboy_adventure_with_a_milf_2445