Naïve Sugar Baby



What’s your gender? Woman
How old are you? 18
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? Europe
What country and/or city do you live in? Madrid (Spain)
Highest education received: Not graduated from high-school
What’s your occupation? Baby sitter
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Naïve
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

Naïve Sugar Baby

How long ago did this hookup happen? 1 month

What was your relationship status at the time? Single

How would you best classify this hookup? Paid sex

How long did you know the person before this hookup? Just met that day

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? A few months ago, my mum and I had many unexpected (and unavoidable) expenses and we got behind with the rent; our landlord (who is a well-known loan shark and a notorious thug) threatened to kick us out if we didn’t pay off the following month (which meant paying two monthly payments in one). There was no way we could get that kind of money in such short notice; my mum works as a cleaning lady and, still in high-school, I try to make as much as possible babysitting. After I told my friend about our financial situation, she told me about a “sugar babies” web platform, an online dating service meant for relationships between successful mature men and young women willing to get paid to keep them “company.”

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went to my friend’s house, she made me put on a couple of her dresses (which, of course, she could have never afforded before meeting her “sugar daddy”), she took some sexy pictures of me and helped me make my own profile (mostly copying hers).

I got my first message a couple of days later. I was pleasantly surprised because the guy was younger than my friend’s, in his early forties, and he was fit and attractive. In his own subtle way, he was pretty straight-forward; not ever mentioning sex at all, in his third or fourth message he offered me to “join” him in a “cozy” place where we could “have a good time” together. By that time I was really scared of what I was doing, but our situation was desperate, so I went ahead and asked him what our “agreement” would be (I had seen Yesika’s conversations with her “daddy”); he offered me 300 euros for an evening together, so it seemed I had got a better deal than her: younger, hotter guy, and not having to spend the night with him.

The date was going to take place exactly one week after our conversation, which meant I spent the whole time anxious, panicky (and, sometimes, I must admit, excited with anticipation). Yesika had insisted on how important it was that I went to date “fully shaved”, something that I had never done before (the legs, of course, but never “down there”). I had no money for a beauty parlor, so I had to do it myself. She also lent me one of the dresses we had used for the pictures, since she said that it was also important that I looked just like in my profile (so much “know-how” made me think that she had more than one “daddy”, which I later confirmed).

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?

The date was not in a normal hotel but in one of those “love hotels” that you can book by the hour. He had booked four hours, which didn’t seem like such a long time (although it was going to be by far the longest time I had ever spent alone with a man). He greeted me at the door and we went inside together; he looked even better than in his profile, he was very elegant, and he smelled really good. It all started very well: he asked me whether I was nervous, and we made small talk until I relaxed a little bit; during our short conversation, he took me by the hand, which made feel a little bit more confident and give him the “I’m ready” look. He took the cue and we started making out very gently, nicer than I had ever experienced. Slowly but surely, he took off all my clothes except for my panties, making sure to go all over every inch of my body with his strong hands.

It was then that the weird things began: he asked me to get on the bed and stand on all fours with my ass outwards. In that position, he pulled down my panties really, really slowly; when they were still around my thighs, he began licking my pussy, my clit, and my ass. He was really good at it and it felt wonderful, but for me things were going too fast, although I couldn’t help getting turned on and wet. After a few minutes, he began fingering me, first with just one finger and then with two. He was so fucking good and made cum really quickly, so I thought things were going well despite all: already an orgasm and we hadn’t even fucked.

He lay down on the bed beside me and we made out for a while. He caressed my body all over. He was very good with his hands. I took his cock and began stroking it, but he said “no” and asked me to get on my knees next to the bed. It wasn’t my first blowjob, but I was still a bit self-conscious of my “abilities”. Anyway, he spent almost the whole time telling me how he wanted it (and reminding me to always look him in the eyes in the act): just little kisses and licks until his cock got wet and he pulled his skin back, then mostly licking and sucking the tip, very, very slowly. It took so long that I was getting tired and sore, but it was nice to see how much he was enjoying it. After probably more than half an hour, his breathing got faster and heavier, so I motioned to take it out and finish him off with my hand, but he probably knew I would do that and was prepared to hold my head down. “Look me in the eyes!”, he commanded once again as he squirted inside my mouth; it was the first time I took a man’s load in my mouth… and it was A LOT. I felt nauseated and wanted to go to the restroom and spit it all but, still holding my head, he told me to swallow it. I almost puked, but I was afraid things could get nasty if I did, so I finally managed not to. He could see I was in tears, but he told me to lick all the remains of cum on his cock and wouldn’t let me stop until it got soft.

I wanted to leave, but by that moment I knew we weren’t going to be done until the four hours he had booked were gone. With his cum still on my tongue, he made out with me. His kissed all over my body and it felt good, which made me feel bad; I didn’t want to like him or what he was doing to me, but he was much better than anyone I had been with before. I regained my calm in a few minutes; I hated myself because I was getting turned on (he was getting hard again, too). I realized we were probably going to fuck already (and I was right… but not yet). He told me to follow him to the shower, where he asked me to choose the water temperature which was more pleasant for me. After being a total thoughtless, rude jerk, he was behaving like a gentleman again (it seemed as if getting close to his climax had made his animal side come out).

We made out in the shower for a long time, with the warm water falling on us. The feeling of our wet bodies rubbing against each other felt great. I was still a bit sick in my stomach after having swallowed his cum, but I was getting really horny. He made me turn around and began spreading shower gel all over my body, as if he was washing me clean, but at the same time giving me a pleasant massage. Then he started fingering my ass; it was the first time someone got “in there”, but his finger and my ass were all slippery with so much soap, so it slid in me quite nicely and it actually felt nice. Once I got used to it, he put two fingers in me, trying to go as deep as possible. It was a bit uncomfortable, but pleasant at the same time, and I kind of just let him do, but I shouldn’t have; when I thought he was going to stop, I felt the tip of his cock and, before I could utter a “no”, he slid it inside of me. I tried to get away, but I was between him and the wall, and he was really strong; he pinned me against the wall and fucked my ass, very gently and very slowly but trying to get as deep as possible. It felt as if I was being ripped apart; I was screaming in agony but, far from stopping, my crying seemed to make him even hornier and the more I whined the harder he fucked me. After what seemed even longer than the blowjob, I felt him squirting inside of me, burning me inside.

When he let go of me, my legs were so weak that I dropped on the floor while he just washed his cock, left me there and went into the room to watch TV while I recovered. I felt so miserable that I just wanted to leave, so I gathered all my strength and went to get my clothes. He just kept on watching TV while I put back on the borrowed sexy underwear and dress, determining myself not to wear anything like that again, never to do anything like this anymore.
When I headed for the door, he reminded me that he hadn’t given me my money; I almost kept on walking so as not to have to look at his face again, but we really needed that money. He had it in his hand and I just needed to grab it and go away but, as soon as I took it, he pushed me onto the bed and held my legs firmly. He was really strong, and I couldn’t free myself. I was really, really scared but, ironically, excited at the same time.

Once I understood there was no escaping from him, he left my feet on top of his shoulders, pulled down my panties to my knees and penetrated me. I then realized that, after almost three hours in that hotel room, I still hadn’t had his cock in my pussy (that is, I had had the opportunity to get away without actually having “regular” sexual intercourse with him). Now he was inside me, and without protection.

At first, I tried to just think about something else and wait for him to finish, but after a couple of minutes, I started hating myself… because I was enjoying it. I tried to avoid moaning or any expression of pleasure, but he was so good, his cock felt wonderful inside of me. I didn’t want to cum, but he gave me an orgasm in just a few minutes. I couldn’t believe he was hard again for the third time in three hours (and he hadn’t taken anything, because he had lost his erection after his first and second times), but that meant that this third time he was going to last much longer than the other two… which meant that, after seeing me cum, he began thrusting his cock harder and harder inside of me. I knew he was in good shape, but this was too much. He made me cum again and, while I recovered from it, he pushed me to the head of the bed and began fucking me missionary. He went for a kiss, which I didn’t want, but he managed to stick his tongue in my mouth and eventually, as I started feeling a new orgasm building inside of me, I ended up making out with him. He gave me my third orgasm in a row (fourth, after fingering me in the beginning) and a couple of minutes later he ejaculated inside of me. It was the first time I experienced the sensation of having cum inside my pussy, and it felt good, especially when he slid out of me and I could feel it trickling outside. He lay down beside me and we made out for a little while until we got a call from the front desk to warn us that the time was almost up.

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? I hated him and myself for having surrendered one more time… and for having enjoyed it. I was also a little bit worried about getting pregnant; even though there couldn’t be much of it in his third cum, I still got tested a couple of days later (it came out negative).
Funnily enough, as I got up to look for my panties, I could see that he was getting hard again. He actually had the courage to tell me that he’d be contacting me to get together again in a few weeks. I blocked him as soon as I got home. Then I gave the money to my mum (no questions asked) and went to my room to wash my mouth, shower, put some lotion on my pussy and my ass, and cry myself to sleep.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, I was feeling lonely, Submission / Relinquishing power, Making new friends, Peer pressure, Didn’t want to disappoint my partner, Material rewards (gifts, money, drinks, dinner…), Boredom, It was easy / convenient, I didn’t want it but was unable to stop it

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? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? Just my friend.

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? Very

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

Do you regret this hookup? Somewhat

Why do you regret this hookup? I really didn’t know what I was getting into. I think that, in the case of gullible young girls like myself, these well-off mature men take advantage of our naivety and our dire situation to exploit and manipulate us and use our bodies for their own pleasure.

What was the BEST thing about this hookup? Probably the best sex of my life so far, despite everything.

What was the WORST thing about this hookup? He treated me badly.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I still think casual sex is fun (and I will pursue it as often as I can), but I won’t use it again as a means of getting money.

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

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

Anything else you want to add about this hookup? The one friend with whom I shared this experience (because she was the one that suggested this option to me in order to get the money I needed, and that had already been with other men from the same platform) thinks that these men use their hookup dates with young girls so as to boost their ego. In my own particular experience, I believe he didn’t need anything like that: I think he’s just a man who feels attracted to teenagers and uses his purchasing power to get to use them sexually without been frowned upon for flirting with girls who could be his daughter.

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 think that women (especially teenage girls) should be more open-minded, and mature men who are attracted to girls like me shouldn’t be frowned upon; it’s natural and there’s nothing wrong with it as long as sex is consensual.

What do you think about the Casual Sex Project? Great stories! Some of them make me so horny!

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