My First Time With An Older Woman



What’s your gender? Woman
How old are you? 27
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? Engaged/Married (monogamous)
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? Several
How many hookup stories have you here posted before? 1

My First Time With An Older Woman

How long ago did this hookup happen? 9 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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? She was a sexy older woman in her mid forties. She has a fit curvy body with very large breasts and a sexy ass. Her skin was freckled but tan and she has bright green eyes.
I’m a petite slender brunette, I have a lean dancers body with small breasts and cute ass.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?  It was the summer before I was to go off to college. I had just broken up with my high school boyfriend figuring there was no point since we would be going different colleges. I woke up that morning with plans to go to the mall with my best friend but she cancelled on me. But I still wanted to go to the mall since I wanted to by new clothes for college and yes I wanted to get some sexy new underwear. I put on a cute little sun dress and left after breakfast.
I got to the mall and window shopped a bit before I found some clothes I liked.
After a while I got hungry and decided I would get lunch then go to Victoria’s Secret and find some cute underwear.
I got some food at the food court and started looking for a table. Then I hear a voice cry out, “come sit hear beautiful.”
I turned rather stunned and I see a beautiful auburn haired older woman smiling at me. She slid out the chair across from her with her leg. I felt very shy but I sat anyway without saying anything.
“I’m Lauren.” She introduced herself.
“I’m Audrey.” I blushed.
“What’s a hot young thing like you doing hear all alone?” she asked.
“I was supposed to come with my friend, but she cancelled and I still wanted to shop,” I explained. “I’m almost done, after lunch I just have to go to Victoria’s Secret,” I explained.
She gave me a wicked smile and said “I have to go there too, we can go together.”
We had a nice lunch and I relaxed as we got to know each other. I was nervous talking to an older stranger but she was friendly and I soon felt very comfortable and a bit turned on. As nice as she was she still was looking at me the same way guys usually look at me. After lunch we got up and she took my hand and we walked the mall. As we walked I noticed how stunning she was. Her short skirt and heels showed off her amazingly toned legs and her blouse revealed a plethora of cleavage which made me glance down at my little B-cups with a bit of jealousy.
Once in the store we picked out a bunch of sexy bras and panties. We had lots of fun at the store and there was definitely some flirting…

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? When it was time to go we grabbed our bags and headed for the parking garage. As it turned out, we were parked very close to each other. We got to my car and I put my bags in the trunk. Then she suggested I walk with her to her car. I did. It was a big SUV backed into a spot. She unlocked it and threw her bags on the front passenger seat and then she grabbed around the waist and pulled me to her. Our lips met in a passionate kiss. I was shocked and reluctant, but it was amazing and soon melted in her arms. We kissed for a minute then she opened the back door and pushed me onto the back seat. She climbed in and closed the door behind her. She quickly kissed her way up my right leg as I opened my legs for her revealing my freshly shaved vagina. She began softly licking it. I had experimented with some of my girlfriends in high school but this was so intense. She lapped away and it felt so good. It wasn’t long before I was climaxing. My body shook as I came for her. When I came down from my orgasm she came up to kiss me. She caressed my cheek and gently kissed me. She unbuttoned her blouse revealing her breasts and guided my head to them. I sucked her nipples for a while then she sat up on the back seat and I knelt between her legs. I looked up at her and slid off her pink lacy panties exposing her wet pussy which was topped with a soft sexy triangle of auburn hair. I lightly grazed my tongue against it having a little taste. She was sweet as candy and I went crazy licking away at her sweetness. She came hard and squirted which caught me by surprise but was very sexy. Then she pulled me back to her and we kissed as our hands wandered l slipped off the top of my dress so she could touch my breasts. She commented on how small and perky they were and kissed them adoringly. As we kissed our hands worked their way lower and we each fingered one and other was we kissed. We came one more time and fell back onto the seat.
“I have to go I have plans with my husband.” She said as she fixed her clothes.
She walked me back to my car and gave me one last gentle kiss and we drove off.

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 never saw her again. I think about it all the time. That afternoon I went home and spent a very long time pleasing myself thinking back on the amazing sex with Lauren.

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), Learning new things, experimenting

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? Everyone I ever told about this thought it was very erotic.

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

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? She gave me the best oral I’ve ever had.

What was the WORST thing about this hookup? I didn’t get to see her again.

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

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!