Went to a large convention a while back in Vegas that I was really looking forward to. I knew work would be easy and I'd have plenty of time to hit some bars and meet people. Unfortunately, the trip was becoming a dud as I didn't meet anyone interesting. On the last night I turned to Tinder to see if anyone was around me. Slim pickings, but luckily found someone from out of town that was very close by.
Jen was attending the same conference, and we moved to texting within 30 mins of matching. She was a natural redhead cute yet definitely looked curvy/bigger from the pics. She had a figure but was certainly heavier than I'd usually go for. But the red hair and cute smile got me.
Given the circumstances, intentions are somewhat obvious, but I made it clear I don't have random sex, but still like to have fun. She said she was relieved and thought it would be nice to have a drink. Turns out, she was in the same large hotel, and an hour and a half later we met in the lobby bar and she looked exactly like her pics; cute, very curvy, but also much bigger breasts than I expected. She wore jeans and a black v-neck sweater.
She was from Idaho, 36, single. We had a legitimately good non-sexual conversation over a couple of drinks, then I suggested we go for a walk. As we walked I steered conversation back to intentions and "fun." We were both coy and she finally asked what I meant by "fun without random sex." I told her I don't like having sex with someone I meet in passing, but other fun can be had. Of course she asked for an example of such fun. I responded, "Oh I don't know, maybe I could show you my cock?" She responded, "oh wow, interesting!"
With that, she linked my arm and we continued walking. She seemed comfortable, and being close to her I noticed how good she smelled. I walked us toward the elevators still not sure if she was coming up, as we got there she immediately pressed the up button.
In the long elevator ride I told her how much I wanted to show her, and that I was getting hard. She seemed both bashful and eager, and I was realizing that she was really sexy. Soon we were in my room and I offered her a seat on the couch. She looked at me expecting me to sit as well, but instead I started to quickly undress. I'm fit and Jen was looking my body up and down. I was standing before her in just tented boxers when I pulled them down to let her see my cock as promised.
Her eyes darted between my face and now upward pointing cock tipped with pre-cum. She said she had never seen an uncircumcised penis before, so I gave it a few strokes and the skin retracted revealing the full shiny head. She was now staring intently at it, and asked me to stroke it some more for her. I moved closer and obliged her request for several minutes. I was jerking a foot from her face as she twisted her head to see it from every angle. As much as she was enjoying the show, I was incredibly turned on by this beautiful woman watching me masturbate.
She asked to touch it. Jen used the pre-cum to slide her finger all over the head, then stroked my cock with a firm grip cupping my balls with the other hand.
After perhaps 10 minutes of her skilled hand job, I stepped forward and stuck the tip in the top of her cleavage. She then removed her sweater, pulled down her camisole revealing a pretty lace bra which I unhooked and removed. Her breasts were lovely and huge, much bigger than I'd seen in person before, pale with wide light areolas and pink nipples.