Current location: NZ
Highest education received: College degree (eg., BA, BS)
Occupation: Co. Director
Relationship status: Divorced
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 37
How many hookup stories have you here posted before? 11
His Fantasy Fulfilled
How long ago did this hookup happen? 1 week
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand
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 am a busy divorcee who has been enjoying discovering meeting casual sex partners online as in some of my earlier stories. My one issue is lack of time being busy with work and having primary custody of my children.
I had a week off to go on an overseas beach holiday with my best friend and in the weeks preceding it occurred to me it would be a opportunity to hook up with someone and have some fun. I then thought I should have a look online rather than leave it to chance.
I searched online and found a site where people advertised for sexual meetings in my holiday destination. I read through the numerous ads and one stood out as being well written and a bit humorous and sincere. The guy advertised as a young guy looking for someone to fulfil his fantasy of being with an older woman. It wasn’t particularly my fantasy but I liked his ad and I’m older so I thought why not and sent him a message. He replied quickly and we chatted quite a bit online and exchanged photos. I thought he looked really cute, dark hair, nice eyes, a beard, a nice smile. Normal build, Caucasian American and 24. He liked my photos too so after chatting some more we agreed to a one night hook up during my holiday. We worked out a night that suited and I said I’d message him with a time and hotel room number.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On the day I had to get another hotel room as I was sharing with my friend but got one in the same hotel so just packed a small bag and went to the other room. I debated greeting him in lingerie or a negligee but I might’ve needed to collect him from reception so stayed dressed. As it happened he was able to get into a lift and get to my floor. He messaged me he was there so I opened the door and let him in.
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 looked nice as I expected and he seemed happy too but we were both a bit nervous. We sat on the edge of the bed and each had a glass of wine and just chatted. The good news was he was really great to talk to and the easy interesting conversation helped us both relax. He was educated and well travelled and also very interested in what I had to say so we chatted for quite a while. I figured I would need to move things along so I topped up our drinks and suggested we move up to the top of the bed so we could lie back and relax a bit. Once there I put a leg over his and stroked his arm a bit while we talked more. He responded and as we chatted we kept moving our bodies a little closer and touched a bit more. Then I put my drink down, took his off him too and kissed him. He responded passionately and soon we were kissing and groping and slowly undressing each other. I got his shirt off and he had me down to my black lacy bra and knickers. I unhooked my bra and took it off and he sucked my nipples and held my breasts. His cock was rock hard and I stroked it through his jeans, noticing a large pre-cum wet patch. I undid his jeans and pulled them and his shorts off. He had a lovely good sized cock. He very slowly removed my knickers under which I was fully bare and immediately parted my legs and entered me with a groan. We kissed and fucked and after quite a short time he just stopped thrusting and mainly withdrew. I said ok? And he said he was going to cum but didn’t want to cum too quickly. I told him he’s young he’ll be able to cum again and said just enjoy it, go. He thrust into me 3 more times then came.
After that we cuddled and talked a whole lot more. The whole time gently stroking each other everywhere. After a while I could feel him getting hard again. I went to the bathroom and on the way back had a quick look at myself naked in the mirror, my hair all mussed up. I felt incredibly sexy and thought go out there, give that lovely boy something to remember.
I came out and crawled over the bed to him. I kissed him hard then kissed down his chest and stomach, then kissed his cock before licking its length a few times like a lollipop before taking him in my mouth. I moved my mouth up and down his cock, swirling my tongue and looking him in the eye while he moaned and groaned. He started thrusting into my mouth but instead I stopped and straddled him, guiding his cock inside me. I rode him hard, bouncing on him and he grabbed my hips and thrust hard back. I had a powerful orgasm on top of him which he watched with wide eyes, then I rubbed my clit and bounced some more and had another. He was close and wanted me to ride a little more but I climbed off and got on my hands and knees and said now fuck me from behind. He said yes! And started doing that, 20 seconds later he came.
After that we cuddled and talked some more. Politics travel and sex. He asked me some questions about female orgasm. He’s never been sure if partners are orgasming or not and what to do to help with that. I hope I gave him some useful insights into that.
Did you have an orgasm? Did your partner(s)? Yes, 2 each
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We discussed STI history and both had very recently been checked and showed each other. I take the contraceptive pill. We both enjoyed not needing to use condoms.
What were your REASONS for having this hookup? Fun and sex on holiday for my part. A new experience, it was the biggest age gap ever for me. I enjoyed being/fulfilling his fantasy, he is a really sweet guy.
Were alcohol or drugs involved? If so, how much? A little wine, not much, not drunk.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? He said it would be nice to stay in touch and I should look him up if I’m ever back in his area or vice versa. We’ve messaged a bit since. The reality is I don’t think we’ll talk all that much or see each other again we live far away from each other and theres a big age gap. Also I was kind of having a good time for now because I’m a little bit falling for someone back home and don’t know if it’ll go anywhere but want to see so will probably stop this casual stuff for a bit.
To whom did you talk about the hookup? How did they react? My best friend and travel companion. I had to tell her because I disappeared for the night. I tell her most things anyway but did feel embarrassed telling her about hooking up online with a guy more than 20 years younger than me. She then told her husband he loves that stuff thinks it’s funny. No one else
Was this a consensual and/or wanted experience for you? For your partner? Yes and yes
Do you regret this hookup? If so, why? Not at all, great fun
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing: being someone’s fantasy is a real turn on. Also it was nice to feel in charge/more experienced for a change.
Nothing bad except for feeling a little conflicted as having feelings for the guy back home. We don’t have any kind of serious relationship though – but I wouldn’t tell him this happened.
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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