Longer than I intended, and please excuse my phone typing..
Recently spent an entire day (well I did work too) away at a convention scheming to find a woman up for some fun after work. Purposely open to all types, I just looked for non-married, confident women that were from out of town.
In the AM I went around making small talk, noting which ones I needed to find again in the afternoon. I probably talked to 40 women and wanted to follow to with 11 or 12. The convention had an app that you could connect with people, so I connected with all of them and 8 accepted.
Manged to talk to 6 of them again that afternoon. Couldn't get a good read on any of them, except 2 were in large groups and had work plans that night. The other 4 were all going to the early evening cocktail reception, and I made sure they knew I'd look for them there.
Felt like I was striking out as the first 2 of the 3 I found were with groups of people they already knew. But the third, Cara, I found all by herself with a glass of wine. Shorter dark hair, very pretty face and an appropriate yet form fitting dress, probably early 40s, she was pleased to see me.
Small talk progressed and I was quietly happy to learn we were staying in the same hotel. As the short reception wound down she accepted an invitation to go to a nearby but out of the way restaurant bar (I pre-researched it) for a glass of wine.
We had lots to talk about and were mildly flirty. I steered the convo to dating. We exchanged online dating horror stories, and I told her my best and funniest story was too dirty to tell her. "Oh, now you have to tell me!" Cara declared.
It's a long story, very funny and it hinges on unexpectedly getting cum on a girl's face. Pretending to be reluctant, I told her the story with all the messy details. Cara was laughing and blushing. We were now not only in a good mood, but had sex on our minds.
I suggested we call it a night at 9 and we walked back to the hotel. I had a high floor room and when in the elevator suggested I show her the view.
I immediately removed her dress and bra when we got in the room, but she kept her panties on saying that wouldn't be tonight. She had a great mom bod and kept in shape. She proceeded to give me a long and outstanding blow job. When planning a night like this I always refrain from cumming for a week, take my vitamins and hydrate.. just in case.
Asking to cum on a girl's face on a first date is far from a sure bet. But considering her reaction to my earlier story, her eager blowjob, and the fact that I had extremely full balls, I confidently suggested it. To my delight she instantly agreed.
It was one of my biggest loads. And if I do say so myself, I'm damn good at accuracy, getting each spurt on on the face. Given how pent up I was, I knew the first shot could go far, so I held her head close and and aimed at her nose. The next thicker but shorter shots landed perfectly on her cheeks and forehead. I stroked and squeezed the last drops onto her chin.
She leaned back laughing, looking quite pleased. I put my cock to her lips and she gently took it in her mouth again. In my final act of boldness, I asked if she wanted to try it. "At this point, why not?" she laughed. I used my semi hard cock to push a large blob of semen from her cheek into her mouth. She suddenly stood up to look in the mirror and laughed while scraping a long white steak off her forehead with her finger, then licking it off. With my encouragement she ended up eating more than half of the substantial mess.
So even though I didn't get to fuck that night, it probably went better than I had hoped for. Planning pays off.
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