Getting Paid To Have Sex With My Boss

by Ally

What’s your gender? Woman
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: High school diploma
What’s your occupation? Housekeeper
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? Faithfully Married
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

Getting Paid To Have Sex With My Boss

How long ago did this hookup happen? 3 years 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 6 months

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? He’s 6’ 5”, early 60s, gray hair, fit for his age & my boss.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I became pregnant at 18 and got married. Both families helped. We live rent free in a small house the in-laws own and my dad got my husband an entry level job at the plant. The pay is decent but we are barely getting by. I looked online for housekeeping jobs that paid cash and got jobs instantly. My mom and mother-in-law help with child care.

I started out taking on more than I could handle. I was cleaning up for lazy people with a house full of dogs and cats and teenagers. The pay wasn’t very good compared with the amount of effort and complaining I was dealing with. I walked away from 2 houses due to frustration. I was about to call it quits all together until I noticed an add for a housekeeper and it was for an older man that was a widower. The add requested a trustworthy housekeeper and on occasion cook light meals. The pay range was already double any of the jobs I had.

The next day I set up an interview. I noticed the house was big for someone living alone and during the interview told me his wife passed away 6 years ago and he was retired military and worked part-time as a consultant. They had one son that never married and was killed in action in the middle east 10 years ago. This was their dream house and his wife loved keeping it up so he could never sell it. He showed me around and it would mostly be light cleaning. He did require at least 4 hours per day but the pay would be much better than any of my other houses. He hired me on the spot and I quit my other obligations as soon as I got in my car to leave.

The job was easy and I think the guy was just lonely. When I arrived he would ask me to join him for tea and we would talk. I felt like I wasn’t working but he would insist on paying me the full amount. A few weeks had passed and the routine was, I would arrive and have tea, do light cleaning and laundry, cook a light lunch, join him for lunch, clean kitchen and leave. I got to know him well and felt comfortable around him. He would request me to do extra like windows and pay me extra.

I arrived at his house one day a little stressed. Over tea, I told him my husband’s car was in the shop and we didn’t have the money to get it out. He offered to give me the money. I told him I couldn’t accept it. He explained that it wouldn’t be a gift. He would like an extra service in return. I was shocked. He told he would pay me half the amount I needed for oral or the entire amount for oral and sex. I was shocked at this offer. I didn’t want to make him mad and quit because I would have to go back to finding other work. Being polite I told him I would think about it. I was working laundry and got a phone call from the garage. The car was ready. If we didn’t pick it up they would charge us per day for storage. I had made my mind up.

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? I found my boss and told him I was ready to earn the extra money. His face lit up like a Christmas tree. We went to his bedroom. He asked if there were any terms of an agreement. I told him I would give him oral and he could have sex with me. Just regular sex. I told him I was on birth control but I prefer he not finish inside me because that’s reserved for my husband and we have an active sex life and he might find out later. He asked if he could finish in my mouth. I quickly replied, “Don’t press your luck. Just not inside me.” He agreed.

He took off his pants and his cock was semi-hard. I could tell he was already bigger than my husband so I began to suck him. It didn’t take long and he was hard. I laid on my back on his bed and asked if he could give me oral. I agreed. Then, he started out. He began slow but picked up the pace. After a few minutes, I was surprised that I was getting in the mood. I had an orgasm then he rammed himself inside me deep and began to cum inside me. I was a little upset he did that but after his warm sperm began flooding me I was glad he did.

I ran to the bathroom and cleaned up. I finished my regular day’s work and when it was time to leave he paid me the amount I asked plus some extra. He thanked me and told me we can make that arrangement anytime I wish. I could tell he’d had a good time so I gave him a deep kiss on the mouth and said, “Deal.”

How sexually satisfying was this hookup? Somewhat

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? I’ve been having sex with my boss for extra money for 3 years now. At first, I felt bad because I was cheating on my husband but after a few times, I realized it was just sex. I have no emotional connection with my boss and my husband doesn’t have to find out. The extra money has helped us get through rough patches too.

It’s nice my boss still treats me with respect and not like a ‘hooker’. He never asks or pressures me to have sex. The arrangement is we only have sex if I need to make extra money.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Material rewards (gifts, money, drinks, dinner…)

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? Somewhat

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

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? Society and our religious organizations raise us to believe sex is something only for married couples. Most people would label me as a ‘whore’ or ‘hooker’ for getting paid to have sex with my boss.

What was the BEST thing about this hookup? How easy it was to make extra money by using my body. This was the start. We now have sex often and he’s good. It sounds awful but on occasion, I enjoy rough sex.

What was the WORST thing about this hookup? I feel like I’m cheating on my husband. I know if he found out our marriage would be over. Both families would be mad because they’ve helped us so much.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I never thought I would take money for sex but I was put in a position to and with someone I knew and comfortable being around. It worked out.

What I’m doing is no different than a woman sleeping with her boss for a promotion.

It wasn’t like I was walking the streets begging some random guy to have sex with me for money.

All things considered, how POSITIVE was this experience? A little positive

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

What do you think about the Casual Sex Project? This is a great idea to release something that’s been bothering me for years now. I’m not in a position to talk with anyone about my situation. I reviewed other stories and some are similar. After I typed my story and proofread it, I felt some relief. It felt like I had told a good friend.

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