Mature & Beautiful


This post is sponsored by Trust Massage Oil.


What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professional
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? No
How many sexual partners have you had in your life (including oral sex)? Many
How many hookup stories have you here posted before? None

Mature and Beautiful

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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

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? My partner was a warm, caring, mature woman 25 years older than he (I was 49, she was 74). She looked like a woman her age, a plain woman who lived honestly and loved her family. We met via social media, though not a dating site, and discovered that we lived close to each other. It was a time in each of our lives when we were alone and open to new friendships, she widowed for about 15 years and me recently divorced.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began with conversation, first on-line and then on the phone. Our conversation was intimate. She talked about how she withdrew socially after the death of her husband, taking ten years to finally go on-line and make friends. I talked about how alone I felt after my divorce.

After a time we decided to make love. The prospect was very exciting – for her, it was the prospect of a younger man delighting in her; for me, it was delighting in an emotionally mature, psychologically stable, and morally honest woman – someone truly beautiful.

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? We met first for lunch, so we could get to know each other and to give her a chance to back out if she had concerns. We had a wonderful date – others seeing us must have imagined that I was a doting sun, not afraid to show gentlemanly public displays of affection toward someone they must have assumed to be my mother. She seduced me with her smile.

Our first encounter was brief but very loving. She was married for over 40 years and she had a wonderful life with her husband. She made love to me the same way she must have made life to her husband – with all her heart and soul, offering her body for our mutual pleasure.

We cuddled for a time and kissed passionately, Despite her age, she was very voluptuous. She enjoyed when I took her breasts into my mouth and softly moaned as I suckled them. We then undressed and cuddled and kissed, as I played with her pussy. As I said, she was very generous in lovemaking, offering her body joyfully. Her pussy was very wet and warm and I came quickly when she invited me in.

It was a beautiful encounter, but short – her daughter had insisted that we go see her so she could ensure her mom was safe.

We did have one other encounter, where I brought her to my home. We had a wonderful, uninterrupted afternoon and I was able to hold and his my lover for ages as I played with her pussy and gave her orgasms. We also had a change to indulge some things she had never experienced – doggy style, her on top, taking me orally.

She loved being on top, despite some difficulty due to age. She completely enjoyed taking my cock in her mouth though she was reluctant to bring me to orgasm that way. So she invited me to finish in her pussy, as I had before.

She was exhausted at the end because she had made love as if she might never do it again. Because of her age and circumstances, she very deliberately let go of any inhibitions she had and made love passionately. No young woman could ever match her authenticity, her joy, and her beauty!

I am remarried now and will not stray, and my lover now struggles with her memory. It’s unlikely that we will be together again, but i still dream about being her young lover.

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? I still remember her fondly and she is still my friend, as is her daughter. The day after, I wanted to do it again though I knew a relationship wasn’t in the cards.

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

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, I was feeling lonely, 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. It was a beautiful friendship with two encounters, and i regret not being able to share it.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The intimacy with someone who showed me that maturity is beautiful!

What was the WORST thing about this hookup? That it couldn’t be public and on-going. WE would be judged harshly and I am not prepared to care for someone 25 years older than me.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve always regarded sex as beautifully intimate and have always preferred beautiful maturity to vacuous youth. My experience confirmed those feelings.

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

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

Anything else you want to add about this hookup? No

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? The sex, though it happened quickly, was not at all casual. Sex is an act of spiritual and emotional entanglement,

What do you think about the Casual Sex Project? It is wonderful to finally tell my story of loving an elderly woman

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