First Time Trying Anal

by Ebenezor

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? UK
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Manager
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Seeking better sex than I get from my wife
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 3

First Time Trying Anal

How long ago did this hookup happen? 4 years ago

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For less than a year

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? Abi is a pretty, short-ish girl in her 30s with long dark hair, big inviting brown eyes, and curves in all the right places. Her tits were a perfect size. I don’t care what cup size they were, but they were large, firm, and she had enormously sensitive nipples. She also has a peachy little bum and a small tattoo on her back. We had been having an affair since shortly after we met.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We hooked up whenever we could, usually in hotels where I was staying for work, and occasionally at her place when her flatmate wasn’t around. We would make the arrangements each week.

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? This happened in the same hotel that we had originally hooked up in. It remained our favorite – and a regular venue. I still cannot pass it without thinking of her. It became a hallmark of our relationship.

While we had had regular vaginal and occasional oral sex, she wanted to have anal sex this time. It was not something that I had ever really tried. I had tried to get my wife to try it many years ago, but we abandoned the attempt and she made it clear that it wasn’t something that she liked or wanted to ever do again. So this was a new thing for me.

Abi had even gone to the trouble of procuring some dark towels to put on the bed (I actually paid for them). We had regular vaginal sex – missionary, her on top, and from behind. She had come many times as usual and was dripping wet. I used the lubrication from her pussy to apply to her anus and my cock. I’d held off from coming especially since I knew I had to be extra hard to get inside her ass.

After guiding me and applying more lube I felt her sphincter relax and I was inside her ass! It felt a bit different from her pussy. All of the grip was at the entrance with less on the rest of my cock. She asked me to go slowly at first, but I was soon able to get up quite a rhythm. What I hadn’t anticipated, was just how much she was into it. She moaned loudly, was playing with her clit and came at least 2 or 3 times. Also – as a bonus – I was able to carry on fucking her while she came. Unlike regular sex when she seizes up and almost pushes me out of her.

Eventually, I felt my climax rising and I came inside her ass. No need to worry about birth control either. Although when I withdrew, things were a little messy and I went straight to the bathroom to clean up.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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 continued to hook up on and off, and this arrangement lasted for over 4 years. We did anal on a more regular basis, but always with condoms after this time. It was ironic that we were both more careful about using them for anal than vaginal sex, even at times when she wasn’t on the pill.

She was really into anal and I think would like to have done it more, but she sensed I was ambivalent about it (which was true). It was fun, but I actually preferred her pussy, she felt amazing.

We broke up just over six months ago and she is now in a full-time relationship. In fact, they are now living together. I do still miss her a bit and I will always love her a little. We share the odd secret email. I think she misses me too a bit but we will never hook up again.

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), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, To cheer myself up

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 didn’t tell anyone specifically about this hookup, but a couple of close friends know about the affair.

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? Somewhat

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I got to properly try anal sex for the first time and bareback. I don’t know if I will ever get the chance again.

What was the WORST thing about this hookup? The mess!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The affair changed the way I felt about my marriage and my wife. I may post more about that in the future.

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

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

Anything else you want to add about this hookup? I had never realized how much some women are in to anal. I think it’s a minority, but still.

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? For many years, casual sex was my outlet to staying in a marriage where the sex was infrequent and awful, but it is not a long term fix. Although I had fun (and so did my partners!).

What do you think about the Casual Sex Project? I am becoming addicted to the better stories!

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