I Went from Soft to Hard

by Anal Enticement
Gender: Male

Age: 36
Race/ethnicity: Caucasian
Location: USA
Highest education received: College degree (eg., BA, BS)
Occupation: Self-employed
Religious affiliation: Atheist
How religious are you? Not at all
What best describes your sexual orientation? Heterosexual
How many hookup stories have you here posted before? 0


I Went from Soft to Hard

How long ago did this hookup happen? 2 years

How would you best classify this hookup? Friends with Benefits

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? She was average height, blonde shoulder length hair. She had smaller breasts and a nice round ass. She really was the college girl next door.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was at her apartment after our first date. We met for drinks and then she invited me back in.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? She was drunk and all over me. I was honestly not that into it. I don’t usually go for women who throw themselves at me. I was not getting hard. She pulled out my dick, forcefully and was sucking on it desperately to try and get me going. I was seriously going to go home. Then she asked me what I wanted. I thought about it and said anal. For some reason at the time it seemed like fun. Like I could dominate her and she would do whatever I wanted. She said yes and that was it. I fucked her so hard for awhile, she loved it. Then I bent her over and slid it right into her ass. I think it hurt her. She did not even make a noise. I finished and fell asleep. I woke up the next morning to her taking off my boxers and blowing me. She really was a very sexual girl. Always horny.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We discussed but did not use any protection.

What were your REASONS for having this hookup? I was recently single and wanting to have fun.

Were alcohol or drugs involved? If so, how much? We were both drunk, her much more than me.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We sort of dated briefly for about a month. She kind of became obsessed. She would show up at my place randomly. I then started seeing someone else and she would not stop contacting me for about 6 months.

To whom did you talk about the hookup? How did they react? I told a small group of my guy friends. They could not believe that she let me fuck her in the ass and it was the first night we even met.

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? Not at all

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about her was her willingness to do anything I wanted. She even did anal to mouth. She was very dirty which was surprising because she looked so innocent. She was the last girl I had sex with before I got married so I think it got any and all of my final fantasies out of me.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

What did you think about this story? Tell us in the comments – just be nice!

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