MY FIRST TIME (ANAL) [FM]

Since my last story, I’ve realized there are tons of people on reddit that want to hear about my anal stories… I thought I’d start out by telling you all about my first time, which was about 4 years ago now with a guy I met off Tinder named Steve…
Steve lives two hours away in another city. I had just downloaded Tinder, not knowing what to expect and not really understanding the purpose of the app. I was about 26 at the time, Steve was my first match. After Steve, I had about 4-500 matches in the span of like two days and decided to delete the app because I didn’t like all the attention. I guess I was like fresh meat for the Tinder world.
Before deleting the app, I gave Steve my number, told him I’m deleting the app and if he wanted, he could text me. He texted me immediately, and we continued to text nonstop for about a week. Initially the conversation was very innocent, but one night I was lonely in bed and I decided to message him how badly I wished he was there with me. He began to tell me all the things he would do to make me feel good and we started FaceTiming and he watched me play with myself until the point of climax.
The next morning he messaged me that he couldn’t stop thinking about me and he desperately wanted to see me in person. He got us a hotel room halfway between my city and his, and I was to meet him there in a few hours. I spent the entire morning shaving and oiling myself up. I did my makeup, put on a cute black lingerie set, a sundress and sunglasses, and left the house to meet my first Tinder hook up.

Now, at this point I was fairly vanilla in the bedroom. The only man that I had really ever been with lasted a total of 30 seconds to two minutes, if I was lucky (I wish I exaggerating).

I met Steve in the parking lot of this very rustic looking hotel that was on the water, he was very handsome. He was about 6’2, very muscular, hazel eyes, black hair brushed back. I ran in to his arms and hugged him, he squeezed me and just breathed me in, telling me I smelled and looked amazing. It felt very natural, I was comfortable with him. We held hands and walked up to the hotel, checked in and went up to our room. The door hadn’t shut yet, and he had me pinned against the wall. He stared me up and down, slid his hand up the back of my thigh, and grabbed my ass hard. He could tell I was breathing hard, a bit nervous, so he brushed my hair behind my ear, still pinned against the wall, and asked me if I was scared. I told him I was a bit nervous, and he just looked deep in to my eyes and said I had nothing to worry about, that he was going to make sure I left happy and satisfied, and then he held my face with his hand and kissed me. He tasted like mint. We continued to kiss in the doorway, me against the wall, his body pressing harder and harder on to me for a couple minutes. Then he stopped, scooped me up, carried me over to the bed and sat me down. We continued to kiss some more, and he slowly started kissing my neck and shoulders, slipping the straps of my dress and bra off as he went.

He asked me to move up in the bed, laid me on my back, as he sat by my feet. Looking back, I don’t think he had a foot fetish, but I did think he knew exactly how to get me to relax. He began removing my heels one at a time. He massaged and kissed my feet and started working his way up my calves and thighs. I still had my dress on, so he slowly started moving my dress up, giving him access to my throbbing, waxed pussy covered by my sheer blank panties.

He looked like he was in another world. It was just him and my pussy, I wasn’t there. He started lightly outlining the lines of my lips and gently kissing my inner thighs. He’d pick a spot, gently rub it with his thumb, and then kiss it, gently sucking on my thigh before releasing and finding another spot, all while using his other finger to stroke the slit of my pussy. I just lay there in slow torture and watched him discover me. He began slowly licking along my panty lines, first one side, then the other… by this point I was soaking wet, and when he went to stroke my slit again, he could feel my wetness oozing out of my pussy and dampening my panties. He smiled. Whatever he was doing was working. He was a god damn sorcerer or something, I swear.

He asked me to raise my hips, and placed a pillow under my lower back. My hips were elevated off the bed now, and it gave him much more access to my pussy. Now that I think about it, it gave him access to my asshole too. With this positioning, it was much easier for him to remove my panties… he slowly pulled them down to expose my bare, wet pussy. I’ve always been proud of the way my pussy looks. It’s very cute, clean looking, almost cartoon like. He kept praising what a pretty pussy I had, before diving in with his nose and licking me up. He lay his chin at the base of my pussy, and slipped his tongue deep between my lips. With slow, long licks, he lapped up all my juices before using his fingers to separate my lips and tickle my clit with his tongue. It felt amazing. It was the first time I had been eaten out like that. I was extremely self conscious at first. Every time my ex would eat me out, he’d go and wash his mouth out because he hated the taste of pussy. Steve was not like that at all. He told me my pussy was the best he’s ever tried, and after watching him indulge himself, I relaxed and trusted I must taste fine.

[Side note, ladies, if a man does not like eating pussy, do not let him eat yours because he’ll make you feel like something is wrong with you when he’s the one with the problem :)]

Anyways, Steve watched my face as he played with me. He could tell I was thoroughly enjoying myself. At one point, I threw my head back closed my eyes, and just focused on the feeling of his tongue playing with my clit and his fingers rubbing up and down my slit… he paused for a second, probably to watch my face, and slowly inserted his pinky in to my pussy. We locked eyes, and I could tell he was equally as surprised as me. He didn’t expect me to be as tight as I was. My pussy was wrapped around his pinky so tightly, he could barely move it. “Fuck! You’re so fucking tight!” I laughed a little and it became obvious he was worried about hurting me. He began fucking me with this pinky, and licking and sucking my clit again. This continued for a few minutes and I could feel him trying to switch from his pinky to his index finger, and then slowly trying to force two fingers in. It was a very slow process… but he was patient.

He began slow, and when he felt my breathing relax a bit, he started picking up pace. It was my first real orgasm. Before Steve, my ex would either finish before I came, or wouldn’t encourage me to ride out my orgasm. Not Steve. He wanted me to ride it all out, and when I told him I was cumming, he told me it was okay, and continued to finger me and flick my clit until I had the most amazing orgasm. My entire body convulsed for what felt like an entire minute. He slowed down… kissed my inner thigh, pulled his fingers out, and cupped my pussy to help me calm down. I never told him that was my first real orgasm, but I’m sure he knew.
We took a break to drink water, have a protein bar, and chit chat. After 30 minutes of this, we were back at it again. This time I sat him down on the edge of the bed. I sat on the ground between his legs and while I was tying my hair up, he pulled his dick out of his shorts and began patting my head, brushing my hair back for me. I honestly can’t remember how big he was but I’m pretty sure he was a bit bigger than average, nothing crazy. BUT… he had a very nice curve. At the time I knew nothing about being on top and making myself climax, but if we ever hooked up again, I would take full advantage of that curved dick.

I gave him a very long, very very sloppy blow job. I had spit mixed with precum dribbling down my chin, and he loved the view. He kept telling me what a good girl I was and telling me he wanted to watch me take it all down my throat. I didn’t care that I was choking and couldn’t breathe, I wanted him to know how much I appreciated him. At one point, he told me to look at him in his eyes, he grabbed my ponytail, and shoved his entire dick down my throat and held it there. My eyes filled with tears, and my mascara began running down my face before he released me and did it again. I loved it. I loved every second of this man fucking my face. When he got close to cumming, he pulled his dick out of my mouth and kissed the top of my head. He told me to sit on his face and 69 him. I obliged and sat on top of his face in reverse. I couldn’t help but moan the entire time I sucked his dick because of how good he ate me out. I was still so sensitive from before but it felt amazing. He was fingering me and eating me, while I was literally choking on his dick.

At one point, I felt him stop and spit on my asshole… that was a very new experience for me and I just kind of froze. He continued eating my pussy, and I continued deep throating him. While he was eating me, he slowly started using his thumb to massage my anus. Again, very new experience for me but it felt incredible. I moaned harder with his dick in my throat. He took that as a sign to continue and he continued apply a bit more pressure as he massaged my ass. Eventually it went from him eating my pussy and playing with my ass to eating my ass and playing with my pussy. I loved it. I had no idea how much I would love this feeling. At that time, eating ass was not something anyone ever talked about. I didn’t even know it was a thing. Steve quickly made me realize how much I had been missing out on. He told me to stop sucking his dick and instead he sat behind me while I lay there, head down ass up in doggy style. He was eating my ass and playing with my pussy. Slowly he started using one hand to massage my pussy, with he used his other hand to massage my ass. He spit on me again and rubbed my anus with his thumb in a circular motion and then in one quick motion, his thumb was inside me. It took me a second to realize because I was so relaxed.
He continued rubbing my pussy with the other hand and Fucking me with his thumb in my ass for a few minutes until he slid his finger out to insert his index and ring finger. I shoved my head deeper in to the bed and raised my ass more in the air for him to finger me harder. It felt amazing. He continued spitting on me and I’m pretty sure at one point he threw some lube on there because the next thing I knew, he was mounting me from behind, pulled his fingers out, told me to play with my clit, and he slowly put his dick in my ass. By the time his dick was entering me, he had been warming up my ass for a good hour, and it was nicely oiled up so when he put his dick in… it felt Fucking amazing. I loved every second of it. After a few minutes of him slowly moving in and out of me, and my body adjusting to his size… he started going harder and just fucked my ass sooo good. He hadn’t cum at all the entire time we were together and I could tell he was starting to get in pain. He asked me where he could cum, probably hoping I’d beg him to fill up my ass, but instead I said on my back. He started fucking me very hard, pounding me and driving my head deeper and deeper in to the bed, until I felt him tense up, pull out, and shoot his entire load all over my back. I lay there as he quickly grabbed napkins and cleaned me up. Then we went and showered together, had an amazing dinner, and both headed home like nothing happened.

We’ve stayed in touch all these years but I never saw him again.

Source: reddit.com/r/gonewildstories/comments/hi9nfb/my_first_time_anal_fm