What’s your gender? Man
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What’s your sexual orientation? Heterosexual
How long ago did this hookup happen? Yesterday afternoon
What was your relationship status at the time? In a relationship (monogamous)
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? Carrie was in her mid 30s, shoulder length brown hair, amazing brown eyes, sort of average body but a very nice ass. Never hooked up before this. She was a friend of a girl I used to hook up with. Never met her in person just talked on the phone
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Carrie ran her own cleaning business and I had reached out to her to come by and clean my house a couple times a month. We have never really met in person just talked over the phone. I would leave the house unlocked for her and she would come clean. She asked that no one be home when she cleaned as it helped her not to work around people. She came to the house yesterday and I went out on the boat. I was only about halfway out on the lake and realized I forgot my wallet. I headed back to the house. I walked inside and seen her bent over mopping the floor. She had on a pair of grey yoga pants and a sweater her ass looked really great in the yoga pants. I startled her a bit when I walked in. She was very attractive and it kind of surprised me. I walked over and shook her hand as this was the first time we had officially met. I told her I would be out of the way shortly I just needed to find my wallet quick. She said ok and went back to cleaning. I grabbed my wallet off the nightstand and headed back upstairs. I stopped to talk to her some more. I asked how her business was going and she said not so great, she only had a few clients and most only wanted her there one time a month or so and only a few hours at that. I usually had her at my place for about 4 hours for a deep cleaning. She was charging $50 an hour to clean which was not unreasonable at all. I told her I was sorry to hear that and asked if there was anything I could do. She jokingly made a comment about paying her more money. I laughed with her too but got a thought in my head. I asked if she was serious about the extra money. She stopped cleaning for a moment and said yes with a kind of confused look. I told her to hear me out and if she said no I would never bring it up again. She said ok. I told her I used to have a cleaning lady come in and clean before her. I had found her on craigslist. She would come to the house and clean in a bikini and a couple of times topless. I told her I paid her a pretty decent amount to do that too. She still stood there with a confused or maybe a disgusted look on her face I couldnt really tell. She asked if I was seriously asking her to clean like that. I said if she wanted to I would double her pay to $100 an hour instead. She said no to me. I said ok I wouldn’t bring it up anymore. I went to the bathroom quick and then was about to head out the door. she asked me if i was serious about doubling her pay. I said yes. She said she could really use the money and agreed to clean the house in her bra and panties for $125 an hour. I told her sure. She asked if I meant today and I said yes. She said ok and went into the bathroom. I grabbed a seat on the couch and waited. She came nervously walking out of the bathroom in a Victoria’s Secret bra and panties red in color.
Damn, she looked amazing it made my dick jump. She slowly walked over to the kitchen and began to clean again. I watched her movements the whole time. Her ass was perfect. I asked if she worked out a lot. She asked why. I said her ass was amazing and I loved her body. That seemed to make her a little less nervous and she got back into cleaning like normal. I was rock hard in my pants by the time she got to the living room. She got pretty red in the face I’m guessing she must have seen my bulge. She got the vacuum out and had just plugged it in when I stopped her. I asked her how she was feeling. She said she was kind of nervous but also excited as I was watching her every movement. I asked if she wanted to make a little more money. Again there was that nervous look of hers. I asked if she wanted to clean naked and I would give her a $100 on top of the $500 for today. She thought about it a minute and agreed to. She removed her bra first. She had some decent sized breasts, pretty average in appearance. She then began to pull down her panties. I stopped her and asked her to face away from me as she did it. She said ok and turned with her back to me. She bent over and pulled down her panties. She had a nicely shaven pussy and her ass was so hot. She began to clean the living room and I just watched everything she did. She stopped cleaning and was red in the face again. I asked what was wrong and she asked why I was rubbing myself. I guess I hadnt eve.mn realized I was doing it. I apologized to her for that. She said she actually didnt mind it just caught her off guard. I asked her if she still wanted to make more money. She didnt get that nervous look this time. She asked what she had to do. I said I would give her another $100 if she would come suck on my dick. She shot back with $200. I said deal. I didnt give her much time to reconsider and pulled down my shorts and my dick sprang out. She slowly walked over to me and got down in front of me. She said so $800 total for today right. I said yes. She said ok.
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? Carrie reached out and gave my cock a few strokes. She then. Spit on her hand and it ran her hand down my cock. She did this a couple more times. She then stroked me again but lightly so her hand would glide over my cock. She looked up at me as she took me in her mouth. She seemed pretty experienced in giving head and it felt great. She used a lot of tongue and spit. She was able to take almost my full length when she deep throated me. She cupped my balls and rubbed them too. It felt really great but I honestly wanted to fuck her at this point. I asked her to get on top of my cock. She pulled her mouth off my cock with a smacking noise. She said it would be another $200. I said that’s fine. She sucked me a couple more seconds and then stood up. She crawled on top of me on the couch. She lined me up with her hole and slid down onto my dick. It felt so great to be in her. She rode me hard and fast once she found her rhythm. It felt great. She ended up leaning down and we kissed while we fucked. I grabbed her ass and forced her down deeper. she tensed up and squeezed my neck hard as she came on top of me. I could feel her juices running down me. She apologized and said she was a squirter. I didn’t mind that one bit. I asked to get behind her. We walked over to the kitchen table and I bent her over it. I pushed into her from behind and began to really rail her. I spit on my index finger and circled her asshole with it. She moaned and didn’t object so I pushed my finger inside of her. She tensed up on my finger when I did but didn’t ask me to stop. I asked if she was into anal. She said normally no. She said she doesn’t mind having it played with while having sex though. I asked what her price would be and she said like $500. I moved in from that subject because anal isn’t worth that much. She moaned as I continued to slam her from behind. I could feel my balls begging for release and knew I was close. I grabbed her hips and pushed in real deep as I shot my load. I emptied in her and then pulled out. I sat down on the couch. I was still hard and asked her to come back over to me. She walked over and stood there. I asked her to get on top again. She said it would cost more. I decided I was good then. She seemed a little sad I didn’t say yes to her. She finished cleaning the house naked for me. I kept watching her and stroking myself a bit. She kept me hard the entire time. When she was all done I got some money for her. I handed her the $1000 I owed her. She was extremely happy to get that money.
She asked if I was still wanting to fuck one more time. I said yes. She said she was down to fuck again and said not to worry about money as I had already paid her for sex. She said she honestly didn’t think she would get the entire amount from me. I took her into the bedroom this time. She sucked on my dick some more before she laid down and entered her missionary. We fucked for only a few minutes before she came and squirted again. I could feel her juices dripping down my cock and down onto her. I started to pull the way out so just the tip was in her and then press back in. This felt amazing and she seemed to really enjoy it and she came again. She apologized and said she was just really turned on from all that money. She pulled me down to her and we kissed some as I kept up what I was doing. She told me she was really horny and if I wanted I could put it in her ass right now. I didn’t ask if she was sure. I pulled out and ran my dick along her to gather some juices. She had cum running out of her pussy from me from before along with all of hers that she had squirted out. I reached down and grabbed a glob of my cum by her pussy and rubbed it on her asshole and my dick. I then pressed until I slid inside of her. I was pretty close to cumming already so I had to hold back. I slammed her ass in missionary as we kissed. I couldn’t take it anymore and blew my load into her ass. I pulled out and laid down next to her. She kissed me again and crawled off the bed. She went to the bathroom to clean up. She never came back in the room I just heard her leave.
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? She texted me the next morning and thanked me for the business. She asked if she could count on me for future visits to keep her business. I said yes. She then asked if it would be like yesterday every time. I said it didn’t have to be. She sent back she liked the money but understood and would be happy to keep cleaning for me. I shot back she cleaned me very well. She sent back a smiley face
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), Power / Dominance
How intoxicated were you? Not at all (no alcohol or drugs)
How intoxicated was your partner? I don’t know
How wanted was this hookup for you at the time? Very
To whom did you talk about the hookup? How did they react? My buddy. He asked for her her number to come clean for him
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? I don’t know / I’m not sure
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? It was a great scenario that played out between us and she was attractive
What was the WORST thing about this hookup? Cost a lot of money
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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