Inexperienced Sugar Baby



What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Madrid, Spain
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Show business
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Ephebophile
How many sexual partners have you had in your life (including oral sex)? Around 50
How many hookup stories have you here posted before? 0

Inexperienced Sugar Baby

How long ago did this hookup happen? 1 month

What was your relationship status at the time? Engaged/Married (monogamous)

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? I met her in a sugar daddy / sugar baby social network. She wasn’t really my type and she seemed rather inexperienced, but she assured me that she had had previous encounters with other sugar daddies before and they had all been satisfied with her. Also, she was quite eager to get together and she was a teen, which was what I was looking for, so I ended up agreeing to meet her for a couple of hours in a love hotel. She said that she was 19 and studying her second year of Medicine. When I met her in person, she did look that age physically, but she was too naïve for being in university, so I guessed that maybe she was self-conscious of being still in high-school at her age or that perhaps she was underage and afraid I wouldn’t want to be with her if I found out (although it seemed very unlikely that she was below the age of consent, which is 16 in Spain).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I tried to make a little bit of small talk while I walked her to the hotel, but she was either too shy or unwilling to have a conversation, so I began making out with her as soon as we went into the room and proceeded to strip her of her clothes almost immediately. As I have mentioned before, she wasn’t my type, but I must admit that she had a very nice body which would delight fans of large breasts and tanned skin. She wasn’t very receptive to kissing, caressing, massaging her breasts or playing with her nipples, so I told her to lie down in bed. I put a pillow on the floor, knelt down with my head between her thighs and began giving her oral. Her response changed completely and she began breathing heavily and massaging her breasts, which I loved to watch. She also had a gorgeous vulva, a very tiny innie, my favorite kind; the only drawback was that she wasn’t completely shaved, which made licking and sucking a bit uncomfortable.
I didn’t seem to be able to really turn her on just by licking her vulva and her clitty, so I began thrusting my tongue in her pussy. Boy, that completely changed the scenario! I realized that she was more vaginal than clitoral, so I decided to stop giving her oral and finger her. She was really wet by then, but so tight that, even with just one finger, I had to slide it in very slowly. Nevertheless, as soon as I began fingering her, I could feel how her pussy went from “really wet” to “soaking wet” (to the point of dripping on my hand and the sheets), so I went ahead with a second finger, which made her start moaning really loud, something that really, really turns me on.
The way she moaned, massaged her breasts and rocked her body to move along with my fingers gave me the impression that an orgasm was building up inside of her, so I decided to keep on fingering her until she came. I made her lie on her side and tuck her legs so that her pussy would be as tight and sensitive as possible. That did the trick and after a couple of minutes of hard fingering and G spot rubbing her moaning got really, really loud, her body began trembling and in the end, it tightened as she gasped for air.
I hadn’t even taken off any of my clothes yet, not even my shoes, and she just lay there motionless, still breathing heavily and softly caressing her own breasts, so I just got naked while she recovered, lay down beside her and began making out again. It was a bit disappointing at first, because I was really, really hard and she was barely touching me; when she finally did, it was even more disappointing, because she clearly had no clue about how to do it (which made me wonder that she probably lied about having been with other sugar daddies… or them being satisfied with the encounter), so I just told her to go down on me. It’s always nice to have your cock in a girl’s mouth, but again she was helpless, so I made her kneel down on the same pillow I had used before and indicated her how to do it right. Once “trained”, she proved to be really good at it and brought me to the verge of cumming in less than five minutes. I usually like to finish on the face, but she seemed so naïve (she wasn’t even making eye contact throughout the whole act… which would probably have made me finish sooner) that I was afraid she would overreact and I would have had to spend the rest of the two hours apologizing to her, so I decided not to. She was nicely licking my glans when I really felt the orgasm building; I pushed my cock inside her mouth because I wanted to cum in her mouth, but I didn’t hold her head or anything because I wanted her to feel free to take it out; also, I made a point to be as loud as possible so that there was no doubt that I was going to cum. I was really loud the last minute, so anybody with any experience whatsoever would have realized what was about to happen; then I came hard, really hard, and I ejaculated a lot. I wasn’t even touching her while I came, but she just stayed there motionless, not sucking any more, receiving my load in her mouth. I really wanted her to keep on sucking me until I got soft, but she took my cock out of her mouth and then she really freaked out, almost about to cry, so I just suggested she went to spit it in the toilet and, when she came back, I went to take a leak myself and gave her a few minutes on her own.

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? When I came back, she was sitting down on the bed checking her phone. I lay down beside her and tried to strike up a conversation while caressing her back and her side, but she wasn’t very receptive at all. I told her stuff about myself and asked her questions to break up the ice but to no avail. In the end, as I was beginning to get hard again just by touching and watching her, I just told her to lie down beside me and we began making out again. Despite her inexperience, I really wanted her to ride me so that I could see her big breasts bouncing up and down, so I made her get on top of me. At first she actually “lay” on top of me and didn’t do much else apart from making out, so I guessed I was going to have to do all the work until we started fucking. I slid her body on top of mine until the tip of my cock rested on her vulva so as to do a little bit of foreplay before getting down to business. However, as soon as she felt it there, she asked me if I had a condom (which sounded silly to me, because we were in a love hotel and there were condoms all over the place). Anyway, I took that as a sign that she was ready to go, so I told her to take one from the bedside table, I put it on (with her still literally on top me me) and slid my cock in her pussy. It felt wonderful to be inside her amazingly wet and tight pussy, and she was showing to be enjoying it a lot, too, because she was moaning even louder than when I fingered her. Anyway, she still had me doing all the work and I couldn’t make her sit up and ride me properly. Also, I was finding it hard to slide the whole thing inside of her, since she tried to avoid it, so I guessed that might be a little bit painful for her and stopped trying. Anyhow, just with a little bit of effort from my side, it seemed from her moaning that she was getting a lot of pleasure, so I realized that the position was good for her and I quitted trying to make her sit up and just fucked her in that position as hard as I could (she was barely moving on top of me: but for her moaning, she might as well have been drunk or asleep). After not so long, she began moaning louder and I could feel her pussy tighten around my cock; I was planning on taking it easy and fucking her until the end of our two hours, but the tightness of her pussy felt so pleasant for me that I decided to accompany her and we orgasmed at the same time (hers seemed pretty intense, but mine was just OK).

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? So, in the end, we had the room for like 15 more minutes, which with another person I would normally have spent talking or kissing, but I decided to just take a shower. I did invite her to join me, but she declined. The creepiest part was that being a love hotel, there was a transparent glass between the shower and the room… and she didn’t take her eyes off me throughout the whole shower. But the funniest thing of all was that, when I gave her the allowance before leaving, she actually had the courage to ask for more (as if the encounter had been worth it!) and a few days later she texted me to ask me if I’d like to meet again (no wonder, since apart from the money, she got two intense orgasms in less than two hours without any effort whatsoever from her part!).

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To cheer myself up, Power / Dominance, Boredom, It was easy / convenient

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

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

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? A little bit

Why do you regret this hookup? But for her moaning, it was like fucking a doll.

What was the BEST thing about this hookup? She was very submissive.

What was the WORST thing about this hookup? The fact that I couldn’t break the ice with her.

All things considered, how POSITIVE was this experience? Fairly 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? It’s very important for me; I would fuck a different girl every day if I could.

What do you think about the Casual Sex Project? Fun stories.

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