Iron & Wine

by Andy

What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Portland, ME, USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Legal Advocate
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Strong and playful
How many sexual partners have you had in your life (including oral sex)? >10
How many hookup stories have you here posted before? 0

Iron & Wine

How long ago did this hookup happen? 2 months ago

What was your relationship status at the time? Dating casually

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 had been with my wife for over 10 years, married for some 7 years of that time, when I decided I’d had enough and left her. It hadn’t always been bad, we’d had a lot of good times and two beautiful children. Yet, it’d been almost two years since she’d last told me she loved me or been affectionate in any way. I didn’t want to live that way. I couldn’t continue to live that way. Our divorce – and the struggle surrounding it – hadn’t yet come to an end, but I so desired intimacy and connection and desperately wanted to find something or someone who might give me some hope that things were going to get better. I decided I was ready to try again.

Julie and I met through an online dating app. Not Tinder, but one that holds itself out to be a little more serious and a place where I could potentially meet a good woman. She was beautiful. Standing about 5’5″ with short, dark, hair and striking blue eyes, Julie was like one of those voluptuous fertility dolls with large, firm, breasts and hips that made you think of sex. In her early 30’s, Julie was the mother of three young children and recently divorced from an unappreciative husband. She, too, seemed to have been neglected by love and had many desires to fulfill.

Having met through a dating app, Julie and I texted back and forth for a couple of weeks to get a feel for each other. She was funny and quirky and we seemed to share a lot of beliefs about the world. The distance between us (about an hour) was an annoyance, but we agreed we liked talking to each other enough to accept it. Finally, when we were both satisfied that we probably weren’t being catfished – and, likely, when our sexual innuendos and teasing had gotten us irreparably hot and bothered – we made plans to meet for the first time over dinner.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Julie showed up in a beautiful, short, green, dress with knee-high tan boots. I wore an old collared shirt, jeans, and my work boots. That first meeting we could hardly be bothered to order dinner, laughing and talking for hours until they closed the restaurant and started vacuuming the floors. When it came time to say goodnight I walked her to her car, a minivan filled with cheerios and crayons and car seats.
Palatable in the air, we both knew what the other wanted. We began to kiss and fondle and my hand went up her dress to discover she hadn’t worn any panties for our date. Julie was dripping wet. She pulled me in tight and kissed me as hard as she could. Laughing together, we crawled into her van kicking toys and seats out of the way. Kissing and touching like we were ravenous for each other, I wasted no time putting my hand back inside her dress and fingered her for only a moment before she came, her whole body shaking. She pushed me back into the seat and, on her knees, unzipped my pants and put my dick in her mouth.

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? Almost immediately she moaned and whispered, “God, you taste good.” Moving her head up and down rapidly, with purpose and urgency, she sucked on my dick strong and hard. As she did I reached around her waist and continued to fuck her with my fingers, making her orgasm at least once more while she worked my dick with her mouth.

When she began to stroke my balls with her hands I knew I couldn’t last much longer. I told her I was about to cum and she responded by pushing her head down hard, getting as much of my dick in her mouth as she could.

When I came, I came hard. I can only imagine that my cum shot heavy into the back of her throat with force. She wanted every drop. She swallowed everything I had. When I was done, she put her head down in my lap, my dick still in her mouth, her arms wrapped around my waist, and laid there contentedly. For a while we stayed like that, me stroking her hair and massaging her shoulders as she continued to lightly suck and swallow whatever little bit I had left.

We were finally compelled to end our encounter when her phone rang. The babysitter wanted to make sure Julie was going to be home on time. Looking around us at the crayon-covered walls of the minivan and her children’s school backpacks we embraced and laughed about being lovers and parents and the realities of life.

We both agreed it had been a great time and resolved to see each other again soon.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? Immediately after our encounter, I called to tell her once again how much fun I’d had. I couldn’t get her off my mind for days. My hope moving forward is that we may find something serious and important together but, first thing’s first, I want the two of us to have as much fun as possible.

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), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Being intimate with and feeling wanted by someone I wanted too.

What was the WORST thing about this hookup? The sense or fear that it may very well be short-lived.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

All things considered, how NEGATIVE was this experience? Not at all 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 think safe, casual, sex is a very good thing so long as both partners are on board with the casual aspect. My preference is still to have lots of good sex with just one person in a committed relationship.

What do you think about the Casual Sex Project? I like it.

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