Older Inexperienced Sex Worker



What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Southern Australia
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 0

Older inexperienced sex worker

How long ago did this hookup happen? 15 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Paid sex

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? I was at the end of a long relationship and just broken break up with my first long term girlfriend. I was open to try new experiences that weren’t possible previously. Details were found in the local newspaper. The receptionist on the phone didn’t say too many about the lady working that day. There was a one bedroom unit in a inner city residential block where a lady would be based for the day.It was a 5 mins drive away, so after a quick shower I was ready.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Her unit was a nice area of the city. She answered the door in a modest outfit. Along with making some small talk it took a little while to take in and appreciate her simple beauty, not quite betraying her age. She looked to be southern European origin originally but seemed to have been in Australia for some time. She was dressed casually and simply.

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? After paying for the hour service in cash and going into the bedroom. We each went to a chair in the room and got under dressed. As we were doing so she said, wow you are a bit younger than i was expecting..they said that it would be mature men that visited. However she continued to get undressed and didn’t act reluctant in any way.

After some short foreplay admiring her breasts i lay back on the bed and she put a condom on.
She then gave me a blow job. It was a little awkward and she stopped at one stage to check and ask whether she was doing a good job. I don’t think it was something she had done a lot of previously. It wasn’t the best blowjob but she was enthusiastic and i still encouraged her to keep going.

I was getting excited and pulled her up to my chest and told her to get on top of me. She quickly applied a small amount of lube from a container on the bedside table. She slid onto my cock smoothly and i held her upright as she moved her hips. This is one of may favourite positions being able to watch her move and also play with her breasts. After about 5 mins with her on top she moved faster and intently and very quietly came. She looked to be savouring the moment and then lay down on the pillow next to me. I hadn’t expected that to happen but it was nice. She told me my girlfriend or wife was lucky. I hadn’t much sexual affirmations in my previous relationship so it was a bit surprising to hear that. I moved on top of her missionary style and finished.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? Afterwards she told me that she was recently widowed and faced some financial difficulties. She wasn’t experienced with other men during her marriage and her husband and her had a simple sex life together. I never saw her again but it is one sexual experience I haven’t forgotten.

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

What were your motives for this hookup? Fun, pleasure, horniness

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? Somewhat

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.

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? experiencing an older woman,

What was the WORST thing about this hookup? nothing

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!