What’s your gender? Woman
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Washington, DC
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Unemployed
What’s your current relationship status? Dating casually
Religious affiliation: Jewish
How religious are you? Somewhat
What’s your sexual orientation? Fluid
Any other term(s) that describe your sexuality or sexual identity? Try-sexual (I’ll try anything once)
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 0

It’s the Motherfucking D-O-double-G

How long ago did this hookup happen? Today

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 1 to 3 years

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? *SD (as my best friend and I refer to him…Snoop Dogg…Sugar Daddy..) is a very tall, in shape, white man, age 56. He is currently married with five children (three from a previous marriage and two from his now wife’s pervious marriage). SD and I have known each other for some time now. I worked for him for a brief time a few years prior but our families have been friends for many years (I went to Hebrew school with one of his daughters- just a fun fact for you to put this all in perspective). Before a few days ago I had never thought of him in a sexual way.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My best friend has had an arrangement with SD for about three months now. They see each other occasionally and she gets an allowance. I am the only person she talks to about the arrangement and I fully support her choices. Since SD knows we are best friends he has been insisting on having a threesome with us as he has an attraction to both of us sexy women. While she is my best friend, we have agreed that’s just not in the cards for us.
Recently, I became unemployed and have been struggling to make ends meet. I’ve been doing a few odd jobs here and there just so that I can make enough money to pay my rent. I came home to live with my parents a few weeks ago and have been spending a lot of time with my best friend. Since she tells me everything, I know that she is making a good amount of money just from having sex. I love sex- with men and women. There are few things in this world that I enjoy more. So I got to thinking, what’s one time with SD going hurt? Sure won’t be hurting my bank account and my best friend has been raving about how great he is in bed, so why the hell not?! I proposed the idea to my friend and she instantly texted him saying how he would do anything to get me in bed. Sure enough a few minuets later I had a text from SD asking if I wanted to grab coffee and chat. I told him I wouldn’t be in town for much longer and was hoping to just go ahead with everything. I felt very informed thanks to my best friend and I knew that he knew what he was doing. This wasn’t his first rodeo. We texted for a bit and then he told me to sleep on it and let him know in the morning. That night I decided to watch some porn videos of women with older men just to see what I was getting myself into. I was instantly turned on and knew I was down. The next morning I confirmed and he booked a hotel room for us. We talked a bit about our limitations, what we like and don’t like and sent a few pictures to get more comfortable.

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? He told me to meet him in the back parking lot of the hotel at 10am. I got there and hopped in his car to go smoke a joint and chat a bit. One of the things I enjoy more than sex is smoking weed. Put the two together (and with a little caffeine in my system) and I’m in heaven. While we were driving and smoking we had a casual friendly conversation. I tried to not let on that I was very nervous. I tried to keep the conversation as non sexual as possible as I puffed on the joint. Once I was feeling pleasantly high on marijuana and caffeine I was ready to go through with it. We got to the hotel room and we continued chatting, sitting on separate chairs. While we talked I could tell SD was checking me out. I then stood up to take off my coat, trying to get more comfortable and SD said, “You know I’ve always found you so sexy. From the first time you walked into the office I’ve wanted you.” This made me feel good. He then stood and began to touch and admire my body. I have to admit- I work extremely hard for my body and am very proud of it. I am a fitness fanatic and health and exercise are important to me. SD told me how much he appreciated all my muscles and curves and how much it turned him on. Having a man tell me that really turned me on too. SD began to kiss me gently and I closed my eyes and tried to quell my thoughts. I told myself that this was a new and exciting experience and it was important to explore this opportunity. We then proceeded to the bedroom. I laid down on the bed with only my leggings on (shirt and bra had come off and left in the other room) and gave him a look that I was ready. He began to kiss and touch me all over. SD kissed my neck and then my nipples then down to my stomach. He kissed and teased the inside of my thighs and I could feel myself getting wet as he purposely kissed everywhere except for my soft, waxed pussy. I told him he was teasing me and that I liked it very much. My best friend had in mind as I began to relax even more. His tongue finally made it to my clit and he began licking and sucking on my wet pussy. I again closed my eyes and first began to picture previous partners while SD ate me out. As he brought me closer and closer to orgasm I decided I needed to just fully surrender and let my thoughts go. Yes, he was 32 years older than I was. Yes, I was getting paid for this. But it did not mean I couldn’t just enjoy the sex, and besides, he knew what he was doing down there! I let out a deep breathe, cleared my mind and just let myself have a very fulfilling orgasm.
Once I caught my breath Snoop exclaimed, “You have amazing orgasms.” More compliments definitely helped my ego and my horniness. He then whispered, “I want you to ride me so I can see your huge tits bouncing up and down.” I pushed him on to the bed next to me and began to lick and suck his very hard penis. At this point I hadn’t decided if I was going to actually have sex with him. I kept that to myself though and figured that when the time came to decide I would know. For now I would show SD how much I LOVE giving head. I am a people pleaser so I looove to make my partner cum. I’ve been told that I am very talented when it comes to sucking cock and this performance was no different. Snoop was blown away (lol) by the way I was working his cock with my tongue, my lips, my hands. I told him that I wanted him to cum for me. He told me to get on top of him and ride him. And so I did- in that moment there was no thought necessary. I rode him slowly at first and then got faster and faster until I came again. I got off of SD and went back to sucking his cock so that I could take a little breather. SD had told me that he loves to make a woman orgasm multiple times and I wasn’t going to say no to that. When he could tell I was ready for more he pushed me down and picked my hips up and began to eat me out again. I came very quickly as I was already so wet and so horny. At this point it was his turn to cum (again, I’m a people pleaser and plus I was there to do a job!) so he entered me with my hips still in the air and he began to fuck me hard this time. It felt great. I could tell he was close to cumming and so I told him I wanted him to cum on my tits. I knew that he would love that and also I didn’t want him cumming inside me despite having an IUD and oh yeah, he’s sterile. After a few more deep pumps inside me, SD pulled out and began to cum on my boobs. He finished and collapsed on the bed. I got up and cleaned myself off.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? After I washed up I came back and sat on the bed. I did not feel like cuddling as my brain instantly went to this being a business transaction and I needed to act professional. I hadn’t thought about that before but in that moment that is how I felt and still feel about it. While my orgasms certainly weren’t fake, I still felt like I had just put on a performance. A very excellent performance I might add! SD was in shock as to my “wild” ways in bed. When you first meet me you would not expect me to 1. smoke as much pot as I do 2. fuck the way that I do. It’s a great feeling to give people something other than what they expect of me.
We both cleaned ourselves up and got dressed. When I came out of the bathroom, SD said, “Now this is the awkward part. I slipped a little something into your pocket.” I thanked him and told him what a great experience that was and we left. We smoked one last time and parted ways. When I got to my car I checked my pockets and instantly thanked my best friend for setting that up and offered her a cut of the money. She said it was all mine. I went right to the bank to deposit my earnings as I felt I should not have that kind of money on me and plus it was making me feel strange about what I had just done. I called another close friend of mine and told her what had just happened and vowed that it would never happen again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) IUD (Intrauterine device), Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, 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? Marijuana, hashish

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Marijuana, hashish

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? My best friend obviously knows and approves as she is the one who set this up. I told my other close friend because I knew she would be honest with me and she told me that I should not do that again. Her feelings were that a true “sugar daddy” buys their “sugar babies” gifts and lavishes them. With SD, all I did was have sex and I was paid for that. She feels it boarders being an escort.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? A little bit

Why do you regret this hookup? If I take this for what it actually was- paid sex where I was the one being paid- then I feel a small sense of regret.

What was the BEST thing about this hookup? The experience and the money.

What was the WORST thing about this hookup? I was paid for sex with a man more than twice my age who is married with children.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Right now I feel slightly guilty that I was paid for sex but at the end of the day what’s done is done and it is not going to happen again.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? The more that I reflect on the experience I feel a bit more positive about what happened. While I will not do it again, I also wouldn’t change the fact that it happened. The sex was fantastic and it is important that I focus on it as that.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I am a huge advocate for casual sex! Sex is amazing and if is something that is important to you than you should be doing it with anybody and everybody! I have had many sexual partners in my 24 years of living and I wouldn’t trade my experiences for anything. And just because I have had many partners and I am a women does not make me a whore or a slut or anything derogatory. I am a human being who loves and appreciates sex. Deal with it, society!

What do you think about the Casual Sex Project? I discovered the Casual Sex Project when reading a recent Daily News article by Zhana Vrangalova. The article was titled “I feel sorry if Kanye likes anal play and doesn’t admit it.” I enjoyed the article and I am very glad it led me to the Casual Sex Project website. I appreciate the community and love finding inspiration in the stories.

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