Amazing Second Date

by J.James

What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? BC
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Carpenter
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 3

Amazing Second Date

How long ago did this hookup happen? 5 years

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? We had met online about 3 weeks before and gone for a coffee and a walk around town, finding out about each other. She was a few years older than me, petite, athletic, professional, divorced with kids at home. I thought she was pretty attractive and probably pretty hot under her casual attire. The first coffee date was successful and we maintained contact during the time I was gone for work: about 3 weeks. Our texting and phone calls were pretty sedated, no sexting or real discussion of sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We agreed to meet for dinner on my way through her hometown. She invited me to her house before we went out. She greeted me with a hug and a quick kiss and offered me a drink. We went out on her deck and chatted, discussing dinner plans and life. She gave me a quick tour of her house and we returned to the kitchen to get ready to go out. She was wearing a casual summer shirt which showed off her muscular arms and shoulders. We started kissing and making out, stroking her arms and pulling her little body into mine..she was undoing my shirt and stroking my chest. I calmly suggested we should go back upstairs to her bedroom. She grabbed my hand and dragged me upstairs. We continued quickly undressing each other, kissing each other all over. She had beautiful perky breasts with small hard nipples, and swimmer’s back and shoulders. As I pulled down her panties I revealed a trimmed dark-haired damp pussy which I started fingering and licking. After extensive oral sex, I came up for air and kisses, teasing her by grinding my cock against her pussy but not penetrating. She whispered that it was her turn, rolled me onto my back, proceeding to suck me. I was getting really close to cumming and told her I was going to fuck her. I asked where her condoms were and she said she had none. I went back down on her pussy and my cock started going soft. I ran to my car to get condoms.

A minute later I returned to her bed and she was casually stroking her clit with a bemused look. As I stripped again she smiled and commented on the opportunity to get me hard again.
It didn’t take much sucking for me to be ready, and I rolled a condom on and slipped into her wet pussy. We fucked missionary style and I quickly came, she held me tightly and rocked me back and forth as went soft inside her.

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? She seemed to have enjoyed the sex and we cuddled. We talked about where we should go for dinner and other topics, me spooning her and stroking her smooth skin, teasing her breasts, gently pinching her nipples. Surprisingly, I felt myself getting hard again and began gently grinding my cock against her ass cheeks. She pushed back and opened her legs as I slid my hand down her body to her pussy, teased her clit and spread her lips fingering her as I kissed the back of her neck.
Soon she rolled me over and started sucking me again till I was fully hard. I put on a fresh condom and she slipped my cock inside her and began riding me. I knew it would last longer the second time and we took our time, fucking with her on top, then missionary and finally finishing with her on her hands and knees bucking under me as I fucked her hard doggy style pulling her hips into me. It was super hot clean sex with a hot 49-year-old. It was my first time with a woman that old and I had no idea of the pent up sexual energy they can have. We fucked once again after dinner and twice the next morning, once as soon as the sun came in the window and we woke up and then again starting in the shower and finishing with her bent over the bed.

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? It was the start of 6 months of ongoing dating and hot sex. It eventually became a relationship and quickly crumbled into rubble.

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

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

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

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

To whom did you talk about the hookup? How did they react? A few friends,
they were happy for me

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

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

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was the first time I realized that the night wasn’t over just because I came once. It led to a great 6 months of dating.

What was the WORST thing about this hookup? Ultimately I ended up treating her poorly and breaking her heart after she became more committed than I was able to be.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes

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

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

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