Yahoo chat rooms were amazing, especially when I traveled for work. This time happened in New Jersey. Mid week, I was back in my hotel after work, I got on my computer snd trolled the local chat rooms. I met a lady, we hit it off, we chatted, flirted a little and then got into sexual conversations. The anonymity that came with the internet really let your freak flag fly.
We chatted a couple days, webcammed, shared pics, and talked, it eventually turned sexual and I asked her “what’s one thing you’ve always wanted to do, that your boyfriend won’t?” She said she always wanted to peg a guy but never had anyone willing, well I quickly said, I was always willing to try something once (can’t knock it unless you try it).
So I suggested she meet me at my hotel bar, I was in an embassy suites so it wasn’t a prince of shit hotel and other people would be there. She agrees, the next day at work I was completely distracted, I get off work go back to the hotel, get ready and head downstairs at 7, we’re supposed to meet at 7:30…7:45p rolls around and I’m thinking I’m getting stood up, not unexpected, it was an internet meet. I ask for the check and she walks into the hotel bar, I recognize her from her pictures, I call her over. We get a drink and talk and I suggest we go upstairs.
We get to the room, I make us another drink, she gets changed and walks into the living room in a dark blue teddy w/ garters. She walks up to me and I start worshipping her body. I stand up and we kiss and slowly walk back to the bedroom while groping each other. She has me lay back in the bed and starts sucking my dick, she gives attention to my balls and gives me a nice rim job. I’ve never had a woman lick my ass and jerk me off at the same time, I was I heaven. She eventually gets up and digs into her bag and gets her strap on ready. She grabs some lube, puts a pillow under my butt/back. She lives up her dildo, fingers my ass with lube asks if I’m ready. I say yes but please go slow. She puts the head of her strapon up to my asshole and slowly starts working it in. It burns, and hurts all at the same time as I’m being penetrated for the first time.
I ask her to go slower, she’s only worked about an inch in at this point, And I’m hurting. She try’s to get more in, but can tell I’m in pain and not enjoying it (I was trying). She says she has a smaller no strap dildo if I wanted to try that. I say yes. She gets that out of her bag, takes off her harness and starts sucking me off again, she slides the slimmer dildo in my ass and I’m in heaven. I needed to start smaller apparently, and she was working my cock and asshole to perfection. I’m on my back, she between my legs working me over and stratells me. I’m rock hard at this point, on my back, and she lines my cock up to her pussy and slides all the way down.
I’m a little freaked out at first because I’m not wearing a condom and I’m balls deep into someone I met in person less than a hour ago. My little head takes over snd I say I’m good and she starts riding me while still working the dildo in my ass. We get a good rhythm going and I tell her I’m going to cum soon, and she keeps riding me and I blow a load in her pussy, after she clenched down hard riding out her orgasm.
We get up and get cleaned up, we had talked before about her spending the night, we get ready for bed and lay down. She sleeps nude so I get naked and hop in bed. Within a couple minutes of laying in bed, I feel her hand rubbing my leg, and makes it’s way over to my Vick, she grabs it and slowly starts jerking me off. I roll/slide closer snd I’m the big spoon at this point. And as she’s stroking me, she moves her ass TM my crotch snd positions my dick on her asshole. She slowly works it in and tells me to go slow, as we’re not using lube. After several minutes, I’m balls deep in her ass, laying on my side and she puts my hand on her neck.
I start to squeeze firmly and pump in and out of her ass. She starts rubbing her clit as I’m fucking her ass and lightly choking her. Eventually she cums and I’m close behind snd fill her ass with my cum. Afterwards, she said she’s never done something like that before w/o lube (okay), but that was great. She ends up falling asleep in my arms, my alarm goes off at 6am, (she knew I had an early meeting), I start rubbing and pinching her nipples, slide my hand down to her clit and start to finger her. She wakes up, I enter her from behind again and we both finish w/in 15 mins, we then get ready for work and leave the hotel.
We got together a couple more times when I was in New Jersey but she eventually moved RJ florida.
Source: reddit.com/r/gonewildstories/comments/k0058a/yahoo_chat_room_stories_i_m_got_pegged_for_the
Interesting story. Gave me a boner ?