Sugar Daddy



What’s your gender? Woman
How old are you? 18
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Burgos
Highest education received: High school diploma
What’s your occupation? Student
What’s your current relationship status? Moving between couples
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Open-minded
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? First one

Sugar Daddy

How long ago did this hookup happen? 4 months

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 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? I had just recently turned 18, and I had been going out with my boyfriend since I was 16. However, I told him right from the beginning I didn’t want to have sex until I became an adult. Even though he’s five years older than me and I knew he had regular sex with his previous girlfriend (who’s five years older than him), he respected my decision and we didn’t have penetrative sex until a few months ago. Of course, we had fun in many other ways before that (petting, oral…) and I “allowed” him to have a fling once in a while so that he could “offload” his natural need for coitus as a man.
We have always shared our fantasies with each other… and made them come true as far as possible. His fantasies are the usual ones for a man: cumming in my mouth, on my face or on my breasts, threesomes… everything sounded ok with me. Two of my main fantasies are very typical as well (and I have already done them with him in these few months): having sex in a public place and having sex in front of other people. My third fantasy is not as typical: I have always fantasized about being an escort, kind of like in “The Girlfriend Experience”. I shared this fantasy with my boyfriend, but I never thought we would do it since it wouldn’t be the same thing if he was my “client”. Also, I wasn’t willing to just place an ad and get in bed with whoever called me (and asking the potential client for pictures, his age, etc. didn’t seem really feasible, as far as I know).
On Fridays, we usually go to a bar where people meet for language exchange, to practice our English… and there’s this man who always stares at me. He’s quite bold: he doesn’t mind whether my boyfriend is around, he just stares at me and, if I look back, he smiles at me but never talks to me. My boyfriend didn’t mind because he thinks that the guy doesn’t stand a chance with me because he’s “old”. For me, yeah, he’s old (he’s 42), but I really think of him as “mature”… and a very attractive and interesting person.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One day, I summoned the courage to ask him why he always looked at me but never said a word. Somehow, he already knew my name, which gave me the creeps, but it was his reply that really caught me off-guard: he said that he wanted to fuck me, but he never fucked underage kids. When I told him I was 18, he just said that I looked much younger than that (I actually do) and that he didn’t want to meddle in my relationship with my boyfriend, anyway.
But that wasn’t the biggest surprise of the day: when I told my boyfriend, word for word, what the guy had just said, completely sure that he’d be outraged, he laughed and told me: “You’ve found a client!” In shock, he took me by the hand, walked me back to the man, introduced himself and told him: “You can have her tonight, 50 euros per hour”. I would have thought he had been caught off-guard, but the man’s reply was really quick: “make it 100 per hour, but not tonight, tomorrow evening, at my place, completely shaved, showered and with clean clothes and underwear”. It outraged me how they were dealing with me as if I was cattle, but somehow his reply made total sense: provided he was also going to shave, shower and put on clean clothes, I’d rather wait until then… which would also give me time to think about it.
I really didn’t care about the money (although he said that he’d pay me as soon as I arrived, before doing anything, and he wanted to be with me for at least three hours), so I had to balance the decision between my desire to fulfill my fantasy and my fear of being alone with a stranger. I was also quite sure that my relationship with my boyfriend would never be the same after that, but it’s not like I was in love with him or anything, so that wasn’t much of an issue (although I didn’t want him to make a fuss of it).

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 was already “completely shaved” as he requested (not that I have much hair down there, anyway), but I showered anyway and borrowed my mom’s little black dress to look more “adult” for him. He had given me money for a cab the day before, “even if you decide not to come” because he lives in a residential community a bit far from the city. I had heard of the place, but I didn’t realize how posh it was until I got there… the cabbie actually opened the door for me, thinking I lived there! His house was the biggest and fanciest in the neighborhood.
A top-model-looking maid opened the door for me and walked me to his room. I guess he’s really straight-forward with these kinds of “affairs” and she’s used to them. She asked me if I wanted “a drink or a bite ‘before’”. That “before” confirms my suspicion that I’m wasn’t the first one in this room.  I was happy to ask her for a cold beer since I was a bit nervous (and excited, too). She came back with the drink, and an envelope containing 300 euros placed on the tray.
I had been expecting him to be wearing a Hugh-Hefner-style robe, just his underpants or maybe even be naked when he came into the room, but he looked more or less like he did in the bar, but his feet were bare. He asked me to stand up and, without saying a word, slowly undressed me while caressing all my body in the process. I didn’t expect it to start so fast, so at first, I was a bit tense, but he was good with his hands, so it didn’t take me long to relax.
Then he asked me to sit on the bed and kneeled down in front of me; he started kissing my inner thighs, slowly but surely heading towards my pussy. After the fast beginning, this seemed a bit slow for what I was used to, but his kisses were wonderful and I was getting wet just from expectation. When he finally got there, I spread my legs as an invitation for him to lick me, but he cruelly made me wait for what seemed like an eternity, just pecking my vulva and licking the surrounding area. His breath so near my pussy made me extremely horny and my whole body was trembling.
The wetness in my pussy was making my labia open like a blooming flower; and as if he had been waiting for that to happen, he gently spread them apart and began licking them so wonderfully. I had been having oral with my boyfriend for a long time, but this was a completely different experience. I wanted him to get to my clit so badly, and I prompted him by moving my hips back and forth but, once again, he gave me the pleasure of the expectation. I thought that, in three hours, we would fuck two or three times, but I was realizing that it was going to be one three-hour fuck.
When he finally reached my clit, I was so ready that it only took him a couple of minutes to make me cum; still, he kept on licking me until I couldn’t bear it anymore and I backed off creeping back onto his bed. The orgasm had left me completely exhausted; I was just lying there, motionless, while he leisurely took off his clothes and showed me his athletic body. He had just shown me how much more experienced he was than my boyfriend, now I could see that he was also bigger… in every way.
He grabbed my hips, slid me towards him on the edge of the bed and placed his cock over my belly, almost reaching my breasts. I should say at this point that I’m rather “petite” (barely 5’0 and 90 pounds), while he was probably ten inches, and very thick. He let me rub it for a while, and it seemed like he wanted to put it in my mouth, but finally, he began rubbing his tip against my pussy.
He pushed me towards the head of the bed and positioned himself between my legs. I was a bit concerned that he might hurt me, so I told him “Be gentle with me… your cock’s kinda big”. I didn’t expect his reply: “As long as you kiss me”. I know escorts are not supposed to kiss their clients, but I wanted it so much, so I held on to his shoulders and greedily stuck my tongue in his mouth; he kissed me back wonderfully while he slowly and gently put his huge rod inside my tiny body. He was so big that I could feel him hitting my cervix, which hurt a little bit but made me even wetter.
We laid almost motionless, just making out and caressing each other for a really long time. He could feel how I could hardly take his cock, so he wanted to make sure that he wouldn’t hurt me when we got down to business. After that long while, little by little, he began gently moving back and forth; he was actually hurting me a tiny little bit (and it hurt to sit for the next couple of days), but I kinda liked it, so I made sure to grab his butt and exaggerate a little bit my pants and whines to encourage him to fuck the shit out of me.
When I finally convinced him that I was doing alright, he held my ankles over my head and fucked me aggressively for a few minutes. This position was tiring for both of us, so after a while, he just rested my calves on his shoulders and continued banging me hard. I loved this position, because he could stroke my breasts and pinch my nipples. Without shifting me, he straightened himself up to rest on his knees and instructed me to play with my boobs while he stimulated my pussy, which by then didn’t need much stimulation. He kept pounding away while I screamed through my second orgasm.
This second orgasm with his huge cock in my pussy and his expert hand on my clit left me sore and exhausted.  I can easily cum twice in a row, but it had never happened to me that fast. I was quite sure I couldn’t go for a third one. I guess my face didn’t look that encouraging any more (after all, we’d been at it for two hours already) because when I was about to offer myself to help him finish with my mouth, he spoke first and instructed me to get “on all fours”. This was the first time I heard someone call it that instead of “doggy style”. I always tell my boyfriend that this position is humiliating for women to maintain a feminist stance, but actually, it’s one of my favorite positions along with the reverse cowgirl. I prayed that it wouldn’t take him too long and I was glad to hear him groan with satisfaction just a couple of minutes later. It was the first time a guy had cum inside my pussy and it made me a bit concerned, but it felt great to feel him squirting inside of me and then feel his spunk dripping out. He told me later that he had a vasectomy, so I didn’t have to worry.

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? We still had one hour left and I hadn’t had enough of his kisses, so I got on top of him and we made out for a while. It didn’t take him too long to get stiff again, and he was clearly trying to get it close to my pussy, which I didn’t want, so I went down on him. It was a bit hard to suck him due to his size, so I mostly licked his tip; he told me he actually enjoyed that more than anything else, so I concentrated on sucking and licking that part. When I could feel he was going to finish, I put it again in my mouth and rubbed his penis until he jerked off on my mouth. He told me not to swallow or spit it out, but to “snowball” him. This was the filthiest sexual act I have ever done, but it really turned me on and I actually got a bit wet and aroused, despite being so sore.
The three hours had gone by and he didn’t seem to be in a hurry. I wanted to stay longer, maybe even the night, but I promised my boyfriend that I would meet him afterward to describe everything, so I took a cab back 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), earning new things, experimenting. I thought it was an important experience to have. To feel better about me. To feel more desirable. To feel more confident. To cheer me up. For the feeling of submission / relinquishing power. For making new friends. Also for material rewards (gifts, money, drinks, dinner…), and boredom. Plus it was easy/convenient

How intoxicated were you? A small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

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? 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 boyfriend is the only person I’ve ever told about this… only about the first time, though. He doesn’t know we been regularly hooking up at his place ever since. Funny how in a few months I have gone from no penetrative sex whatsoever to doing it almost every day: weekends with my boyfriend, weekdays with my “sugar daddy” (he only paid me the first time, though… bummer, LOL). Anyway, my boyfriend started acting weird after this, he keeps asking questions about his size, about how much I enjoyed it… (didn’t tell him the truth). I’m getting a bit fed up with the questions and at the same time, I have a huge crush on my “client” (who, in turn, indulges me and is already treating me like his girlfriend, not caring that I will end up breaking up with my boyfriend to be with him).

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? It made things awkward with my boyfriend.

What was the BEST thing about this hookup? Best sex of my life.

What was the WORST thing about this hookup? It made things awkward with my boyfriend.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m still too young to have an opinion on casual sex; the only thing I know about it is that I love it.

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

All things considered, how NEGATIVE was this experience? A little negative

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 wish people were more open-minded.

What do you think about the Casual Sex Project? Great stories!

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