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I can't make this shit up  

MissDReid 36F
0 posts
9/21/2017 7:45 am
I can't make this shit up


Wanna hear about my most awkward and hilarious experience with casual sex?

Well too bad.

I had been talking to this guy for a few weeks. He said he lived north of Boulder and couldn't host, but his schedule allowed for a lot of flexibility to meet. He said he wanted to take me skydiving. I had never been so I was here for that. And, from the pics he sent, he had a yummy, thick, long dick.

I randomly have some time free up in my schedule so I message him like "I CAN FUCK!" We make arrangements for the night. I offer to pay for a hotel. He thinks it's too much and offers to take me skydiving in the morning to make us even. Sounds good to me!

I pick a hotel halfway between me and Boulder. I let him know where to meet. I'm stuck in horrendous traffic, I message him to say I might be late. He says, "Take your time, I'm coming from north of Red Feather Lakes."

Any readers not in Colorado, here's the geography. Boulder is about an hour away from where I live in Aurora. Long, but not unreasonable. North of Red Feather Lakes is on the border with Wyoming - almost 3 hours away from me!

Okay, so he lied about his location. This will probably be a one time thing which I hate, but that hotel is paid for and we're supposed to go skydiving, so I go. And I'm waiting for him for an hour and a half once I get to the hotel (I pass the time by drinking some tequila), but hey, that dick though.

He gets there finally and I'm basically tearing his clothes off when he walks in. I'm horny as fuck and god am I ready.

I pull his pants down on my knees and my instant reaction is, "...Is this the same guy I was thinking of?" I distinctly remember pics of a nice dick, what's looking at me could not have been more than 3 inches raging hard.

I'm seriously confused and look up to his face, he is very pointedly looking away from me in shame. OH! So those pics were a lie too! What a lovely evening this is turning out to be, and Jesus it gets worse.

I'm still just looking at this dick with half a mind to kick this guy's ass, but hey. I already paid for the hotel and we're here. And skydiving! May as well do the thing.

I start sucking his dick. Now while I've been told my skills are prodigious and guys do not tend to last long with me, I'm about 30 seconds in when I hear him say I'm gonna cum. Wow, a tiny dick AND he doesn't last long? This guy was married and cheating on his wife, how anyone married him and why he would cheat on that saint of a woman... I don't even know.

He promises he can cum and get going again after a little bit. I tell him to just fuck me and then he can rally and we'll go again. And hopefully he lasts longer the second time.

So he's fucking me and ugh is it awful. He's trying way too hard - not to mention it feels like there's nothing inside me. Luckily, it only lasts a minute. I feel like I'm doing a great job of hiding my immense displeasure and I say, "Ok, rally time!"

We're sitting on the bed for a while after, he's furiously jerking off trying to get hard again. After about 10 minutes, he goes to the bathroom and locks the door behind him. Maybe some peace and quiet will help?

After 5 minutes of him being in there, I start to hear some weird noises from the bathroom. I'm a little concerned so I get up to check on him. I lean in to listen and I hear very soft, but very distinct, sobbing.

I have no clue what to do, I want to tell him it's okay (even though it really wasn't), but I settle with just sitting back on the bed and waiting for him to have a good cry.

Another 5 minutes goes by and I hear the door unlock. He comes out, doesn't say a word to me, doesn't look at me. Casually puts his boxers and pants back on, slips on his flip flops, grabs his shirt, and walks out of the room. Shirtless.

I'm just sitting on the bed staring at the door and finally I just think, "Guess I'm not going skydiving..."

AmNoAngel 54F  
443 posts
9/21/2017 1:14 pm

Oh
Em
Gee.
Thanks for sharing Baby.
I promise our time will be better.
And we'll go dutch on the room!!!


MissDReid replies on 9/21/2017 5:27 pm:
Oh beautiful I already knew we'll have all the fun.

bigblackman21221 53M
4080 posts
9/21/2017 1:23 pm

Damn!

Hopefully listen learned.
I wouldn't meet anyone from this site that won't do a video chat first.
They can show you everything that's in the pictures including what they look like.

Try it out.


MissDReid replies on 9/21/2017 5:26 pm:
It wasn't from outcupid.com actually. Otherwise everyone would know who this dude is!

directisma 54M
1 post
9/25/2017 2:45 pm

This is my first blog comment and I normally perfer to keep my crazy thoughts to myself . Here I go...A guy should pay for the room period !! If he is not willing too, then thats a big red flag , dont go! If he can't man up for the room then what next ? Its not all about sex , its about the experience as well . Like having a great evening, followed up by some breakfast and skydiving. It was the experience you wanted !


MissDReid replies on 9/25/2017 5:40 pm:
Eh, I don't mind paying for a room ever. I did mind less than 2 minutes of awful sex.

hornyman4u2nite2 57M

3/20/2018 7:38 am

I'm mostly strait but do love to suck cock every now and then. I have been stood up by men and women, but men are the worst. My giving head fetish is two fold: first I love a heavy cummer, and all guys promise that, but most just don't have it. Second part is that elusive big dick. It either isn't big, or after one blowjob they never "rally" for another round.

I feel your pain.


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