I Was Her Second Man

by Django

What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 0

I Was Her Second Man

How long ago did this hookup happen? 5 months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

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

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? I met her on craigslist. I posted an ad on strictly platonic and she replied to my ad, we started talking and after 3 days we met. She is around my age, slim Asian women with 3 kids but you would not be able to tell that by looking at her body. She looked really HOT. Initially, it was just talking then after complimenting each other all the time we decided to take things to the next level. Sex was out of the question no matter what, because she has been married to her high school sweetheart and has never been with anyone else.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Since we both were married, we tried avoiding meeting in public places. The first time we met in a small park, just walked around and talked. The second time we met again in the same place but that time we end up making out in a car. The third time which was 2 weeks after we first started writing each other we decided to meet in a motel but she kept insisting that sex is still out of question. I knew she liked me so I went along. I got a motel room and as soon as she walked in I knew she wanted to have sex because she was wearing a really sexy summer dress that screamed, “FUCK ME NOW”. I gave her a hug and we started talking than making out and next thing we know, I am on top her taking her dress off. Not only she didn’t mind but she helped me do it.

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? As we were making out and I was licking her B size cups, she kept moaning and telling me how she loves it. I slowly moved my hand down under her panties and started fingering her. She kept moaning louder. I took her panties off and took my clothes off and continued doing what I was doing and next thing I know she whispers in my ear “do you have a condom?” I did bring a condom because I wanted to have sex but I wasn’t sure if she did before we met, so I told her yes and put the condom on. She told me to lay down and relax. She got on top of me and started riding me. She was so tight I almost came, I had to tell to slow down before I blew my load. Then we flipped her on her back and continued fucking her hard. She came once when she was riding me and I came in a condom when I was fucking her. Since we both were sweating we took a quick shower and just chilled and watched TV. After about 20 minutes I got hard again and wanted to go again. She was surprised since her husband only fucks her once. We fucked again different positions until I came. After chilling some more we went again for 3 times but this time she just rode me until she came twice. We both had other plans that day so we took shower and left. It was amazing.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? After she told me she wants to fuck me without a condom and next time we should try something new, like fucking against the well. That’s a different story for a different time. I met her maybe 10 more times after that hookup but we eventually broke things off because she started falling for me and wanted/expected more from me.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, To feel better about myself, Making new friends

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

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? A little bit

Why do you regret this hookup? I regret that she fell in love with me and expected more then I can give her.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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