For the longest time, I told myself I was never going to want to do anal. Even from the time I even started watching porn, to when I lost my virginity, it just never really drew any interest for me. That’s when I met Annie.
Note: this is actually going to be two stories in one – our first hookup and then the anal part (which was our second hookup). I’ll try to speed through the first one.
Crazy story how we met actually. This took place near the beginning of lockdown (early May or so). Like many of us, I had been told that lockdown was going to be a “two weeks to flatten the curve”, then we would slowly return to normal. By the middle of April, we knew that was not going to be the case, that this was going to draw out much longer than expected. So, also like many of us, my mood plummeted and I started to have to find new ways to scratch the social itch.
I’m the type of person that enjoys almost anything active and outdoors. While I was still able to do some of that (long runs around my neighborhood, day hiking trips etc), I really found myself missing companionship. So I turned to dating apps, something that I hadn’t used since my college days. However, I was feeling a bit…let’s call it adventurous (a more realistic term would be desperate, but let’s be glass half-full here), so I started using Facebook dating (yes it is a feature, go look it up). There is a certain clientele that is on Facebook dating, as I was quick to discover, and that clientele isn’t exactly my type although I am a pretty open minded guy.
I was on that site for about 3 days and was ready to give up when I came across Annie’s profile. She was unlike any other person that I had stumbled across, so naturally I was convinced she was catfishing. She was extremely cute, played tennis at a very prestigious college near me, and had a very goofy sense of humor (had a couple puns in her profile, that’s an automatic swipe right for me). So we matched and chatted, all the while I was wary, trying to gauge if she was real.
At her own suggestion, we ended up on a facetime call, and sure enough it was her! We got along super well on the call, so we agreed to meet up for an in-person, socially distanced first date. It was May and the weather had finally turned nice, so we met at a park halfway between us, grabbed some sandwiches and had a picnic. Against both of our initially stated boundaries, we drifted closer and closer together and ended up making out for a good portion of the time.
It was obvious that both of us wanted more, but as we were in a park in the middle of the afternoon, but we needed to move in order to make it happen. My roommates family was staying with us that weekend, so my place was out. And she, being a recent college grad, was still living with her parents so her place was out too. That really only left one option: my back seat.
Don’t get me wrong: the vast majority of the time, I don’t really like hooking up in the car. I don’t mind making out, but I drive a sedan and so there just isn’t enough room to really get comfortable doing anything else. It usually ends up being awkward, it gets very hot (literally like the fogging of the windows). But occasionally, with the right connection and set up, it can be very hot as well. There are a couple of positions that work really well and are a huge turn on.
Regardless, we got in my car and drove to a more isolated part of the park. Without my prompting, Annie started giving me road head, which is awesome but more often than not leads me into some near-death experiences. As I pulled into the spot, I was able to reach down and lift her mini skirt to start playing with her perky little ass, slowly rubbing her clit as well. Pausing for a moment, we both climbed into the backseat. She went first, so I great an amazing close-up view of her pussy and asshole from behind, both perfectly pink, shaved and tight as hell. I found myself wildly aroused, which as I had said before was unusual for me.
Neither of us had a ton of time, so we got right to it in the backseat, wanting to have some fun before leaving. I got her on her back, started licking and fingering her (which no lie is my absolute favorite part of foreplay). My tongue would run in circles over her lips and clit, while two fingers would play around with the inside. She convulsed again and again, moaning and grabbing my head. After a little while, I knew I had to be inside her. I sat upright in the middle seat, while she unrolled the condom and slid it on me, then followed it herself, climbing on top with her tits right in my face. This girl was TIGHT, and it had been a little while so tbh I didn’t last super long. As she rode me, gyrating on top in rhythm to the music still playing from my radio, I pumped all of it into the condom.
We agreed that while it had been fun, it definitely wasn’t enough. Luckily for me, my roommate was going out of town with his family, taking a weekend trip to the beach so I had the apartment to myself. I invited her to come stay the weekend, which just so happened to coincide with my 25th birthday. I hadn’t told her that, but that was unintentional. I typically don’t do very much to celebrate my birthday, so really it had just slipped my mind.
Annie came over Friday night, so we ordered pizza, drank wine, and lay on the couch watching movies. I think both of us were crazy horny, ready to go at it immediately. But there was something about the waiting, the slow build up, the knowing that we didn’t have anywhere to be or anything else going on that just added to the anticipation. By the time the first movie ended and the second one began, we were ready to fuck like rabbits. Making out, I carried her upstairs to my bedroom, her legs wrapped around my waist. She had worn her cutest tennis outfit for me, a sporty tank with a white tennis skirt and no underwear on (it comes with built-in spandex). We lay on my bed, kissing and slowly start to explore each other with our hands, slowly undressing each other piece by piece. I got her top off, and was just started to slide off her skirt, when she stopped me. Looking me dead in the eye, she said
“why did you not tell me it was your birthday???? I would’ve have brought you something special”
“I honestly didn’t think about it. And just you being here is special, we will make it worth it I am sure”.
Wordlessly, she nodded. She then climbed over off the bed, telling me to wait where I was, and she would be right back. Off she trotted, topless with her braid swishing behind her. My mind was racing at this point: what is she getting? Is she super kinky, getting ropes or cuffs or something? Is she just getting another drink? What is going on?
She slips quietly back into the room, all cute, with her hands behind her back and tells me to close my eyes. I agree, and into my lap falls a tube. Not what I was expecting, so I open my eyes and it is a bottle of lube. Not exactly what I was expecting, and to be completely honest, I was confused. Never in all of my hookups had I used lube before: the condom was always lubricated, or (just being real) we had never needed it. I had always made it a priority to get her turned on and wet (like I said, I love eating out and fingering), so it had never been needed. I think my confusion showed on my face, so Annie said
“I saw you staring at my asshole the other day in the car. I want you to put it in there”
“Annie are you sure? I’ve never done anal before”.
I am very honestly not trying to brag, but I am pretty big. Not stature (I’m just under 6′ and about 160, college cross country runner), but I am 8″, even if not particularly girthy. One day I’ll post a picture of myself, but not in this post.
She was certain, so we decided to give it a try. She climbed back on my bed, giving me one last kiss and looked deep into my eyes, before wheeling around and burying her face in my pillows. I slowly took down her skirt, and with her advice, started with my fingers. With the help of saliva and a bit of lube, one finger went in easy. She had done it before, so while she let out a slight moan when I entered her, it was clearly one of pleasure. Since one had worked, I decided to try two. Same result: she moaned slightly, but it went in no problem.
I was getting extremely turned on at this point. I could see her pink clit, feel her constricting around my fingers. After taking my two fingers out, she looked back one more time and said
“Do it babe. I’m ready”
I obliged. Drawing myself up, I lubed up (both me and her) and started to put the tip in. Centimeter by centimeter, I slid in. It was euphoria. She was so tight, that I could really thrust like you would during normal doggy sex. But even the slow motion was driving me nuts. She started making noises, some small whimpers at first but slowly growing louder until she was screaming my name into my pillows. With one hand on her hips, and the other on her back, I started thrusting in and out, ever so slowly, being very clear with her that I would stop the second she asked me to. Instead, she grabbed my hand and guided it towards her tits: the message was clear, play with me as you go in. I was only too happy. I started cupping her tits, playing with her nipples as I continued to slowly go in and out, stopping every few thrusts to just enjoy the tightness.
After a few minutes, I could tell she was spent, so I pulled back out and flipped her over. She was sweaty and clearly in a bit of pain, but smiling like crazy. I knew I needed to finish, but I had to go and wipe off first (not trying to give infections out here), I ran off to the bathroom to leave her to recover while I washed off, and put on a condom.
I came back and she was already spread eagled, eager to have me inside her. We then fucked for a good long time, in a bunch of different positions before I pulled out, ripped off the condom and finished all over her face (as she told me she wanted).
That was just the first of what would be a magical weekend that has completely changed my outlook on anal. Thanks Annie:)
Source: reddit.com/r/gonewildstories/comments/misdi0/a_birthday_analogy_mf
Nice one bro! So have you had more anal since, and with others or?
She is a keeper.