Hook-Up With An Ex

by NIck

What’s your gender? Man
How old are you? 33
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 current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? >30
How many hookup stories have you here posted before? 0

Hook-Up With An Ex

How long ago did this hookup happen? a month ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Sex with an ex

How long did you know the person before this hookup? For more than 3 years

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? Tif and I are from the same small town; we grew up together in the same neighborhood. I took her virginity in high school and ever since then, we have hooked-up often. We were FWB while in college. She was cool because she didn’t mind me dating or hooking-up with anyone else and I didn’t mind when she had a boyfriend. We shared an apartment during my last year of college and was the best roommate a guy could have. She liked to have sex as often as me and was a crazy girl in bed. We had some wild times together. I got a job that required me to move and she wanted to stay and finish her masters. For the next 2 years, we would meet up at the beach for a long weekend of sex. She got serious with a guy and they got married. I never got married and still live the typical bachelor life.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I got transferred to a branch back in my old hometown. It had been around ten years since I had been home and about the same time since I last seen Tif. I was taking a jog on the local greenway, and as I was passing the city park, I heard a familiar voice yelling at me. It was Tif! She came running over to say hi. She looked HOT. She was wearing a tennis dress and sporting the sun visor & ponytail look with tennis shoes. I was embarrassingly sweaty. Her smile was big as we chatted. We quickly caught up with our lives. She pointed at a distance and told me her husband was coaching a soccer team with their kids. She was a mother of three now. She added marriage was good. I told her that I was transferred back in town and was still single. She began to look me up and down. She rubbed my stomach and told me that I looked great and the single women in town will be on the prowl. I returned the compliment. She wanted to give me a big hug but I was too sweaty, and I didn’t want to ruin her outfit. She understood but told me she expected a rain check. Just to be curious if married life and being a mother had changed her, I told her I would love to hook-up with her sometime. I should be shocked at her reply. She grinned and said, “We always did have fun together didn’t we. I’ll tell you what. Let me see what I can do. I have a friend that owes me a babysitting favor. Can I get back with you?” I told her where I lived and gave her my number because I didn’t have my phone. Her reply really got inside my head. I didn’t know if she was trying to get in my head or was being serious.

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? Two days later I got a text from her. She said her friend was able to keep the kids tomorrow from 8 am to noon. I told her that would work. At 8:10 am she was knocking on my door, and soon after, all clothes were off. Her husband doesn’t like giving her oral, so I suggested we start on the bed doing 69. She always gave the best blowjobs, and nothing had changed. I could tell she was enjoying my tongue work too. After that, she got on top and began bouncing up and down on me fast and hard. It was just like before. I squeezed her tits as she had her first orgasm. We had sex four times, and she let me cum inside her each time. She took a shower and before she left she gave me a big kiss and told me that wouldn’t be the last time we did this.

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? We’ve hooked up a few more times. Right now, I don’t see an end to it, and I’m not complaining.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? Nobody

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Having sex with an Ex.

What was the WORST thing about this hookup? Nothing

Anything else you want to add about this hookup? I’ve never used a condom with Tif, and so far we don’t use one. I’ve never asked her about pregnancy protection, but I think she would tell me if it was an issue. She is married, and I’m starting to have thoughts that she shouldn’t be leaving my place full of my cum. I don’t know how to bring up that issue because we don’t have time to talk when she comes over.

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