First Time Anal



What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Educator
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 16
How many hookup stories have you here posted before? 0

First Time Anal

How long ago did this hookup happen? 14 years

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

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

How long did you know the person before this hookup? For 1 to 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? Brandi was a hot MILF. She was short (only about 5 feet tall), had long blonde hair, small tits, shapely hips, and a beautiful ass. She also had gorgeous eyes, a wicked smile, and a slight Southern accent (that became more pronounced when she drank or was turned on).

We worked together at the same high school, and, after flirting with each other for a while, we started fucking pretty regularly. This had been going on for about a year, and she was — without a doubt — the best lover I ever had. Before we started hooking up regularly, she had gone through an extended dry spell (almost seven years — ever since her daughter was born), but once we started connecting, she was eager to make up for lost time. We totally connected in bed, and we communicated our wants and desires openly. This made for mind-blowing sex, including the night we tried anal for the first time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met Brandi and her daughter at a local park. They were there for a night of “Movies in the Park,” and by the time I arrived, the movie was just about over, so they were ready to go home. I put up Brandi’s almost-sleeping daughter in her car seat, gave Brandi a quick kiss, and drove us all back to Brandi’s apartment. By the time we got home, Brandi’s daughter was out cold, so I carried her gingerly up to the apartment and put her to bed. While I was doing this, Brandi excused herself to her bedroom. When I made my way down the hall and into the room, Brandi was already naked and lying on her side, facing the door. She eyed me with those beautiful blue eyes when I came in the door, lightly traced her finger over her already alert nipples and said, “Do you want to fuck me?” I didn’t need to be asked twice.

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? I stripped down as quickly as I could and climbed into bed. Brandi moved to the head of the bed and was flat on her back, legs spread apart. I took a moment to kiss her deeply, suck and lightly bite her nipples (she loved this, and her moans made my already hard cock jump a little), and then move down so I was directly facing her glistening cunt.

I loved eating Brandi out. She had the sweetest tasting pussy I have ever encountered, and I routinely stayed down there until she orgasmed at least once. Tonight was no exception. I began by alternating between licking and flicking her clit with my tongue and then diving deep into her glory hole, trying to fit my entire tongue in there. She bucked her hips against my face while I did this, and I knew she was close to cumming. To put her over the edge, I continued to lick her clit as I inserted two fingers into her twat. The sensations of my tongue on her clit and my fingers rapidly sliding in and out of her pushed her to her first orgasm, and she screamed and grabbed my hair as she came.

I moved back up so we were face-to-face, and — for the first time ever in our relationship — she took my hand and sucked her juices off my fingers. I almost blew my load right there. We kissed deeply again, and she pushed me on my back. Brandi was always willing to “return the favor” when it came to oral sex, and tonight was no exception. She greedily took me in her mouth and jacked my shaft with her hand as her head bobbed up and down on my cock. Her oral skills were amazing, and she knew from experience I was close. Sometimes she would encourage me to blow my load in her mouth, but tonight we both wanted to get to the fucking as quickly as possible. So she released me from her mouth and climbed on top of me.

Her pussy was like a vice, and I loved it when she was on top. She leaned down so I could inhale her gorgeous tits while her hips rocked back and forth on my member. My hands found their way to her ass, and I squeezed and slapped those cheeks as I thrust my hips in rhythm with hers. During all this, one of my fingers found its way to her asshole, and I slowly inserted it. This was not new for us (we’d been experimenting with some anal play for a while), but I could tell she was into it tonight by the way she moaned and locked eyes with me when I did it.

Soon she pushed off me and turned around and got on all fours. We both loved doggy style, and I quickly got on my knees, grabbed her hips, and slowly slid my cock into her beautiful slit. However, after only a few thrusts, she looked back at me and said, “Do it.” I knew exactly what she meant (during our anal play, we’d talked about anal sex), but this was the first time we were really going to do it, and I could still feel my heart pounding in my chest. I pulled out, and she reached around and grabbed my cock, lining it up correctly. She asked me to go slowly, and I obliged. I slowly pushed into her, feeling her ass resist me at first, but then, once I go the head in, open up and accept all of me.

If Brandi’s pussy was the tightest I’d ever felt, then her ass was on an entirely new level. I have always prided myself on how long I could last in bed, but this was so overwhelming (in the best way possible), I knew I wasn’t lasting long. Still, I did my best to hang on, and I drove into her ass while Brandi reached between her legs and alternated between rubbing her clit and playing with my balls.

Before long, Brandi said she’d had enough (this was a new experience for her, too). I slid out of her, and she rolled on her back. In a flash, I was back inside her deliriously tight pussy, and I pounded her hard missionary style until we both came together. I then collapsed beside her, and we finished off the session by kissing, lightly fondling, and smiling at each other.

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? I had to leave shortly after we were done, but I’m not ashamed to admit I jerked off the next morning thinking about how hot the whole experience was. We tried anal sex a few more times after that — but those are stories for a different day.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection

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? Just you. I hope you enjoy my confession!

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Learning it is possible to connect fully with another person (emotionally and physically).

What was the WORST thing about this hookup? Not being with her anymore.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? We are sexual creatures. We should embrace that aspect of ourselves.

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

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

What do you think about the Casual Sex Project? Love it!

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