Humiliated on a Hooup

This is a true story that happened to me a few years ago, just before covid. I've always thought of myself as kinky but had never considered myself submissive until after this.

I'd met Holly on a dating app, she was blonde, a little above average size (but not fat at all) and had absolutely massive tits. We had spoken for a while before going out for dinner. During dinner she had been very flirty, was dressed to show off her tits and reached under the table to rub my cock through my trousers a bit, leaving me rock hard for the rest of the date. Unfortunately she said she had to go see family that evening and couldn't come back to mine after, annoying but it made me really look forward to seeing her again as I was so horny.

It took almost two weeks to arrange to see her again, but in that time we'd sexted a bit and I'd seen some nudes of her. When we went to grab drinks I was absolutely rock hard the whole time, partly at the excitement to get to fuck Holly, but how she was dressed to show off her curves and massive cleavage. All evening Holly would lean over and whisper dirty things she was planning to do to me and gently rub my cock. I reached my hand down between her legs to discover she wasn't wearing underwear and discreetly played with her clit, after a few minutes I could feel her rocking a bit on my hand before letting out a little moan as she came. I thought this might be the moment we went back to hers but she ordered more drinks, and more, until she was very drunk. She went to get an uber but was clearly too drunk so I helped get her home, she asked me to stay as she was cold and we cuddled up in bed. The next morning after we woke up she was grinding her arse against me and said she'd like to thank me for helping her last night, she rolled over and started to rub my cock until I was hard, then went to put a condom on me. However she felt sick and threw up everywhere, which I took as my cue to leave as she got cleaned up.

We again continued to message and she told me all about her fantasies in bed and what we would do when we meet. We met at a bar near hers later in the evening, once again there was dirty talk and her hand wandering down to my cock in the bar.

We got an uber and went back to her flat, immediately making out and had our hands all over each other tearing our clothes off before Holly asks if I'm any good at giving head. I answer of course, push her down onto the bed and go to town on her shaved pussy. She really enjoys it and gets super wet, I use my fingers a bit as well and manage to make Holly cum several times, by the end she was grabbing my hair and pushing my face into her while grinding herself on my tongue to use me. After Holly had cum quite a few times she let go of my hair I looked up and saw her doing a come here motion with her finger, I moved back up and we started to make out again as she rubbed my cock again. After a few minutes she says she didn't realise the time (I'd ended up spending over an hour eating her out over and over again) and that she has to be up early, asking if we could cuddle now and fuck in the morning before she has to go, I'm a bit frustrated after my efforts but agree and we curl up and go to sleep.

The next morning we're woken up by her alarm still spooning, my hands wander to her tits and Holly starts to grind her arse against me to get me hard. I'm thinking I'm finally going to get to fuck her, she turns over and asks if I'll eat her out once more as it got her so wet ready for us to fuck. I agree and this time she jumps up and straddles my face. This is where I really felt like I got used to make her cum as she was riding my face quite aggressively focussing only on making herself cum. After her first orgasm, Holly reaches down to rub my cock through my pants as she keeps riding my face. By this point my face is soaking as she is very very wet and I can feel myself getting close, I try to warn Holly to slow down as I'm about to cum but she can't make out anything I saw given shes sat on my face. I can't hold back any longer and start cumming straight into my pants, to which Holly laughs at me and says I should've told her. Holly picks up the pace of her riding and brings herself to one last orgasm before lifting off and telling me how good that was.

Holly reaches for her phone and exclaims "oh shit" as she realises the time, and says she's going to be late for work and so has to jump in the shower now. She asks if I can leave as shes got about 10-15 minutes to get ready. I'm a bit stunned but agree out of a desire to not want to be rude or pushy. she hurries me to get dressed as she goes and turns the shower on, coming back over to give me a kiss, tell me to message her and give me really quite a hard spank on my arse as she told me I was naughty for not telling her I was gonna cum. I was ushered out the door, made my way out of the building and then the realisation hit me. I'd made her cum what 10? 11 times? and I'm left standing here with a wet face, able to taste her the whole hour journey home by tube and train, and I have pants full of cum. I'd never felt so humiliated, and felt so used, but for some reason it made me want to see Holly again?