Boss’s Secretary!

by Natalie

What’s your gender? Woman
How old are you? 41
What’s your race/ethnicity? Black
What continent do you live on? Europe
What country and/or city do you live in? Paris
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Senior Management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Mostly gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? Married. Wife. Scarred Relationship. Having affairs. Dating casually.
How many sexual partners have you had in your life (including oral sex)? 27
How many hookup stories have you here posted before? 2

Boss’s Secretary!

How long ago did this hookup happen? A week ago.

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Paid sex

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? She was my boss’s secretary or to say personal assistant. I found out she was a bi and that she always did extra jobs after work for extra pay. We met, talked and she accepted my proposal by letting me pay for her time after work. I planned the night for dinner and back to my place for drinks. She was white, 22, slim.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Dinner was casual, she was hot. I rubbed her thighs under the table to get her in the mood. Then we went to the washroom, I kissed her up and tore her panties off. I instigated.

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 I got her back to my place we had drinks and then I pushed her against the wall and kissed the fuck out of her sore lips. I fingered her and carried her up to my room. I undressed, brought out the strapon and fucked her good. Then I performed oral, fingered her ass, licked up the juices, dropped in bed and cuddled miss cutie to bed.

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? Woke up, made out, showered, fingered her, fucked her again, dropped her home.

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), Material rewards (gifts, money, drinks, dinner…)

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Friends. They were supportive.

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? Young pussy, always a thumbs up. She was nice too, good conversations, matured mind, single and available, hardworking.

What was the WORST thing about this hookup? Hoping it would lead us further. Although I’m still in a relationship with my partner we are not on good terms, she is having an affair thus I want to meet others.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It hasn’t.

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

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

Anything else you want to add about this hookup? I would be meeting her on a weekly basis at my home and hers. I will be paying her for the time being until she is stable enough. Sex with her is amazing.

What do you think about the Casual Sex Project? Always turn to here to read stories.

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