What’s your gender? Woman
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Germany
What’s your occupation? student
What’s your current relationship status? Single
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 5

My Anal Defloration

How long ago did this hookup happen? ca. 1 month, just after christmas

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For more than 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? Frank is the father of a high school friend of mine. He is 47, but pretty sporty and still has his full hair. He is tall and a bit hairy.
Frank had seduced me last summer at a party when I was visiting my home town. I live in a different city now, but I visit my parents and high school friends several times a year. You can read about my first experience with Frank in an earlier story.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Last year around christmas time, I started thinking back to my adventure with Frank, the father of a high school friend. He is the first older guy I had a sexual encounter with. I knew that I would have the opportunity to seeing him again as I would visit my parents for Christmas. The memory of that sexy adventure made me horny and I wanted to see Frank again. To turn myself on, I bought some sexy lingerie and send Frank a picture of me wearing it. Frank messaged back saying that he was very keen on seeing me again.

I went to my hometown, stayed with my parents over christmas, messaging and phoning with Frank. We found a time between christmas and new year where he would pick me up with his car. I had told my parents that I would see some friends and come back the next morning.

I put on the lingerie under my normal clothes to feel very sexy and left my parents to meet up with Frank.

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? We immediately started kissing passionately as I got into his car. Frank’s behavior had changed quite a bit. Last time, he presented himself as a confident but tender lover. Now he was really sleazy and full of dirty talk. You could call him dominant. I kind of enjoyed that, even though it was pretty unexpected.

He started off by telling me that he had just taken a Viagra and would fuck my brains out. Then just plainly asked whether I had been a good slut and let many guys fuck me while I had been away. I was a bit shocked at his words (which I cannot translate properly, but will try) but it turned me on at the same time.
I replied that I had indeed been fucking around, So had he, came his reply. Frank asked me whether I had ever been fucked in the arse. I said no, to which he replied that he would change about that. Anal sex was not something on my agenda, but I did not want to stop Frank in his horny tracks by starting a discussion and refusing him. I thought to myself that I d cross that bridge once I come to it.

I took off my clothes straight away as soon as we got into his house, presenting myself in sexy lingerie. Frank admired me and we started making out. Frank said he remembered that I am a blowjob addict and said I should get to work. Startled by his dominance, I simply followed suit, knelt before him on the sofa, got his cock out, and started sucking. While I was giving him head, he kept on talking dirty and telling me how good I was at it, that he was sure that I had experience sucking plenty of cocks. He made me nod to his questions while I was sucking. After a while he had enough of that and told me to get up into the bedroom so he could fuck me.

I was still wearing my lingerie, as I got into the bedroom. Frank got undressed, told me to kiss him, then lie on the bed on my back spreading my legs for him.

I did as he told. He was soon all over me, getting really excited. He slid my undies to the side and licked my shaved pussy. Then he put on a condom (not without mentioning again that this was safer for him because I am doing it with so many guys) and rammed his big cock inside me and started off hammering away. I screamed and moaned. Frank repeatedly demanded to know whether he was doing it to me well. Which he did. I had a massive orgasm as he came inside me.

We made out some more and fueled by the Viagra, Frank got his instrument up again soon. He pulled out some lubricant and told me to get on all fours, doggystyle. I quietly obeyed hoping it would not hurt too much. I just wanted him to have his fun in his dominant way and not interrupt the mood. I felt his fingers inside my anus lubricating me. Frank was breathing heavily behind me as he rubbed his penis against my arse. Then I felt the painful sensation of his dick penetrating my arse. I screamed a bit. He laughed and told me that it is normal but that I would learn to love it. He was a bit rough while fucking my arse, I moaned, this time rather in pain. I let him do it for a little bit, but then I had had enough because it just hurt and I wasn’t getting much out of it.

Frank pulled out and told me that if I wasn’t willing to let him fuck me in the arse, he would not fuck me into my pussy, but into my mouth instead. But since I was a blowjob addict, I’d probably enjoy that. He ordered me to stay on all fours and turn around. Frank started to fuck my mouth, holding my head with one hand and fondling my breasts with the other. I masturbated myself in the process. He kept on talking dirty, telling me how great it is to have a willing young slut like me who would allow him to do anything.
I did not give him a blowjob – he was literally fucking my mouth until he came into it and on my face.

Frank looked at me and laughed, stating that he had done a good job on my face, having covered it with cream more than any other woman’s.

We took a bit of a break from fucking and simply hung out in his place, chatting, eating and having a bit of wine. Frank stopped his dirty talk and dominant behaviour. It had all just been a show, after sex he turned into the adorable father of my high school friend again. The man who had taken us on cycling tours and taught us how to play tennis. We had sex again later on that evening and in the morning. Those times Frank was a tender lover. He got really romantic and asked me whether I would want to stay with him.

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 parted ways again and I went back to the city where I study to celebrate New Year’s Eve with my friends there.
I keep on thinking of Frank’s offer to stay with him. I could study in my home town and my life could be so much easier. But I would probably lose quite a bit of independence.

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, Emotional intimacy, closeness, connection, Power / Dominance, Submission / Relinquishing power, Didn’t want to disappoint my partner

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? 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? I told a female friend in my study city about it. She was very surprised that I have sex with a guy so much older and enjoying it.

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? Not at all

What was the BEST thing about this hookup? Being dominated by a man so much older than I am. I also loved how Frank became the tender lover and person I am familiar with.

What was the WORST thing about this hookup? I didn’t really like the anal to be honest, but I somehow enjoyed the submissive aspect of it.

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

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

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