I Disappointed The Fat Lady



What’s your gender? Man
How old are you? 25
What continent do you live on? Europe
What’s your current relationship status? Single
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 24

I Disappointed The Fat Lady

How long ago did this hookup happen? last week

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a week

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Elke is 46, she is quite chubby. She has huge breasts. She hooks up with guys on a adult dating site.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been quite unsuccessful for a while in my quest to be as promiscuous as possible. So I checked out the older ladies at my adult dating website. I had to realize that they were often rather on the obese end of average.
Finally I get a response from Elke, who lives in my city. I looked at the pics she had sent me trying to tell myself that she is attractive enough.
Elke was happy to have me (as a man 20 years younger than her) over at her place pretty much straight away. A very straightforward hook up.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I show up at her place, Elke opens the door, she is already in lingerie. She complimented me on how handsome I am. I did not know how to reply. We sat down on the sofa and she immediately started to caress and kiss me. I tried to stay focussed on her breasts. I did not enjoy her kisses that much. I played with her titties, I liked that.

We both got naked, and I got more afraid that I might not be able to get aroused. I felt a bit repulsed by her body, to be honest. But I want to be a gentleman and I will certainly not reject any woman that is willing to have sex with me – a holy oath I had sworn as a teenager. Get laid as often as possible and reject no one.

Elke did her best to get me aroused. Blowjob and rubbing my penis with her huge breasts. I got stiff enough to put a condom on.

She presented me her pussy and I really did not want to lick it. I felt ashamed of this, as it is very impolite not to lick a woman’s pussy on that occasion. I tried to shove it in, but my erection failed. I rubbed my penis against her pussy. I got it in for a little bit but then I was not stiff anymore. I decided I cannot do it and I just wanted to leave, as I did not want to spend another 20 minutes desperately trying to satisfy her.

Very ashamed, I got up and get dressed. I apologized, but Elke was very angry at me and kicked me out. I feel very sorry that I have disappointed her.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I just left and rode home. No contact with her anymore.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one, since I felt too ashamed.

Did you get emotionally hurt as a result of this hookup? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? Somewhat

What was the BEST thing about this hookup? The tittyfuck was a bit exciting.

What was the WORST thing about this hookup? Letting Elke down and not properly satisfying her.

All things considered, how POSITIVE was this experience? Not at all positive

All things considered, how NEGATIVE was this experience? Fairly negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I want to have as much casual sex as I possibly can, I will not give up.

What do you think about the Casual Sex Project? Good stories to wank over.

You have a hookup story to share? Submit it here!