[FM] My first time receiving anal. Blissful, but I paid for it the rest of the week

First time we did anal starts about two weeks before we actually did it. We dabbled in some toys, foreplay, and occasionally if there was enough attention given, he would pull out and cum in my ass which is such a turn on I’m having a hard time typing it. The whole plan had me working up to it on my own. I’ll just come right out and say it, anal anything was a deal breaker for me. My boyfriend was the first and only person to do anything to my ass. I loved it. The right setting, mood, and most importantly, the right person, can make all the difference in the world. Because of that I now know I can have intense, blackout inducing, squirting orgasms from anal sex. So, for a little over two weeks I was masturbating after he left for work. We have a big shower with a bench and two detachable shower heads. My technique to help get me ready is fairly simple and I’m sure I’m not the only one who does it.

First was a simple vibrator/shower head on my clit with some gentle touching at my back door. Just the outside until I’m on the verge of cumming which is important for me at least. I stop, then switch the vibrator/SH to my ass to prepare for a little more while I rub myself. I still had to adjust at the time, maybe 3 minutes to get me there. Once I feel properly stimulated I’ll apply some pressure and begin stretching. God I hate saying that. Once I feel the vibrator has done it’s job to get me tingly, I start with fingers and lube. We keep some in the bathroom for shower sex and I probably used 2/3 of it on myself. One finger slowly in and out, then a second. Two fingers is alright, but the oblong shape being wide and flat isn’t my favorite. That being said, two fingers and pressure on my clit is good. I have a smallish vibrator that’s about as long as my palm but semi thick. I do the medium setting and probe a little at a time. Just the tip, the tip and a little more, then some more, all the way to the battery cap in steady smooth strokes. It’s blissful with a shower head focused on my vagina. Then the other toy, the bead wand or whatever it’s actually called. Medium size again all the way until I feel it hitting the curve inside of me. That’s my limit. I would catch myself thinking about doing it while I’m at work and had to run off to the bathroom to tease Dennis. He always responds the same way, dude that’s not cool. Why would you do that to me? To the story…

I brought him to his first day of school last year and we got there early because he had to find his building so better safe than sorry. Now we have just under an hour to kill. We’re talking and I wanted him to notice I wasn’t wearing any panties under my dress. So I made sure my entire leg was exposed as well as my left hip. Kinda hard not to notice. I wanna get to the good stuff so I’ll race through. We ended up fucking in his back seat. His windows are super illegally tinted so we’re good from prying eyes. Wasn’t long, just a quickie before his first day of school. It was only a 50 minute class so I sat at one of the coffee places on campus, one of my friends who lived close by met me. Guys, specifically college guys, don’t stare at people. There’s a certain line where it’s not a compliment anymore and it comes off as creepy. Let’s just say I’m glad I had a lid on my drink. Phone rings and he’s walking out. We head home and we’re just hanging out when I got the idea to initiate my plan. Tonight’s the night. I snuck off pretending to do whatever to grab one of my plugs. I like the medium girth silicone plugs. They’re longer and sit better than the jewel ones. Went in with ease, and it better with me doing all of this prep work. I was changing some of my info on my computer when the plug started to really hit its mark. I had to tease him. I told him I knew something he didn’t know and in his monotone voice, the fucks that mean? I decided to switch to my larger plug which is a jewel one, thicker diameter, thicker stem and it wouldn’t hurt to get a little more prepared. Won’t be in long so no big deal. I’m in my evening attire, my skimpy robe, knee high socks, no panties, and my glasses because I’m blind.

When I was ready, I escorted him into the bedroom and made him wait at the edge while I crawled up to the pillows so he could see what I was hiding. I grabbed my ass with one hand and squeezed so he could see and I said, guess what I’ve been wearing since dinner. With a big smile he said, “the red one?” all impressed. I was trying to sell the moment as best I could so I grabbed the stem and teased myself and asked him to come take it out for me. He pushed me flat on my stomach and began kissing me all over and started to push and pull on it. Compete ecstasy. I felt lightning pass through me. With each push and pull he pulled a little more, and more, and more, and more until I was at the thickest part of the plug which is basically the same size as Dennis. It didn’t hurt, but it was jarring to say the least. I’m thinking to myself I can’t believe I’m about to do this then it was out and I literally felt empty. I got used to it being in for over two hours and he said, this sounds gross but he liked it, seeing me wide open and close up slowly turned him on so much. Who am I to judge, I was the one with a kettlebell up my ass. I told him get the “good lube” and use a lot. He’s applying it and working it in me and on himself and I felt a finger, then a second, then a third. Weird angles, but overall wasn’t bad. The plugs are just smooth and easier to manage but I was ready and I was extremely anxious to try. He did his usual reassurance that if it hurt yadda yadda yadda.

He’s pressing against me and it just went in. There was slight resistance, but it just popped in and that was it. It felt amazing, intense, and all these things at once and I was experiencing a new sensation. This was way more than our toys. He fed more and more until he was damn near all the way in. I can see him in the mirror and half his dick was still out! I though wtf because it felt like he was touching my lungs. Guess that’s part of it. Now it’s a different uncomfortable feeling. Not painful, just odd. So he slowed down and let me adjust. He’s rubbing my clit helping the overall sensation and it was working. I was crazy wet and something about this idea of normal sex that he can just put it in and go versus this preparation, dedication, patience, and buildup for something I was firmly against just a few months ago turned me on. Think about it. You have to go so far out of your way to get here and he did without hurting me once. Slight moments of discomfort, but 99% it’s like an out of body experience. He was so gentle shoving that damn thing in me that I couldn’t wait to get better at it. Then I got into it and that was it, we were having anal sex. I was moaning some things into the pillows, the pleasure was unbelievable and honestly, I wanted him to go as deep as he could. Bottom out in me, I had to know if I could take it. He often reminds me of how dirty I was talking. I do remember saying, it’s making my pussy drip down my legs/thighs. Can’t remember specifics.

I got adventurous and starting touching myself while he fucked me and watching him in the mirror on top of me was otherworldly. His shoulders and arms flexing keeping him above me… makes me shiver thinking about it again. I stashed my vibrator under my pillow for this exact moment. I wanted to feel his dick in my ass and stimulate my clit and holy shit was that fucking intense. I was twitching and clinching all over and then I felt it. I was on the verge of something I was unfamiliar with as that tingling lightheaded feeling was coming. I was loving it and I wanted to feel more. I told him harder and he started hitting it just right. Not too much, just right and I don’t normally swear this much, but motherfucker my ass and pussy began contracting rapidly and I had no idea what was happening. I’ve had orgasms, I’ve anally assisted orgasms, this was something else. My heart was beating so hard it made my vision narrow I thought I was about to pass out. I wasn’t even holding the vibrator at this point, I was just laying on it. I’m making noises I’ve never made and I feel this intense surge come through me and I ended up pulling the sheets off and the only thing keeping me from rolling around was his weight on top of me and his hands holding my neck and side. I’m literally screaming into the pillow and the next thing I know I’m coming to a few seconds later and my stomach and legs are wet. He’s sorta holding me like the snake position in yoga making sure I’m still lucid. Not even close. I blacked out and squirted. I can’t hear anything he’s saying, I just see his lips moving in the mirror then all my sense came back and an aftershock hit me because he was still inside of me and every movement made me feel small little orgasmic symptoms. If I was standing, I would’ve collapsed from being weak in the knees.

We roll onto our sides still inside while I’m catching my breath just kinda collecting myself when he says he’s about to take it out. I was nervous was fuck. I just shook my head and he came out slowly. My ass felt, well different is all I’ll say. I see the wet spot and thought, fuck it no going back now. The thought of squirting made me nervous to lose control like that. Given the current predicament, squirting is no longer an issue. He laid back, I grabbed the lube, reapplied, and got on straddling him. That thing is resting against my entire ass and i think to myself, I’m taking the whole thing. I was determined to take it all. I’m lowering down on him and from this angle, it’s like a different type of sex. Different pressure, different angle, different range of motion, but fuck did it feel amazing. Inch by inch he goes until there’s no more. I’m pretty flexible, yoga helps. I’m slowly riding him and when I get to the top where his sensitive spot is, I would clinch to tighten around him. I’m having fun with it and we’re both getting something out of it. I’m leaking all over his stomach and hips, I don’t even care anymore. Literally leaking like a slow faucet. His hands gripping my hips when I came up was like Morse code for me. I wanted him to cum so bad but I’m not done with him. He went for my clit so I grabbed his hand, sucked his fingers and placed them so they were upwards so I could ride his dick and fingers.

We’re going at it staring at one another lovingly despite the extremely pornographic situation, then that feeling was back. I got excited and though here it comes. Brace yourselves. He knew. He can read me like a book and he told me he wanted me to cum for him. I shook my head yes and I told him I wanted to cum in his mouth. I don’t know why I said that, just felt right. I can hear the lube when I ride him and then these words just kinda came out… “I want you to fill my ass with more than your cock. I need to feel you pulsing. I want to flood your body when you fill my ass.” It’s cringy when thinking back on it but in the moment, oh wee. I wanted it bad. So my ass is filled, his fingers are doing the trick up front, then he uses his other hand to start circling my clit and that felt like I had no bones in my body. I could barely focus enough to maintain my posture. I wanted to pull his hand off but I was holding myself up. Had I let go I would’ve collapsed. It hit me again and I burst like a water balloon. Not that much of course, but I filled his palm and stomach. He pulled me forward so I was braced up against the headboard and he took over driving up into me. The more he went, the longer my orgasm persisted. I feel his wet handprints all over my side and I’m thinking to myself, don’t pass out don’t pass out. It was so good but so much it was hard to talk between my random murmuring. If I black out again I’m crashing into his face and I definitely don’t want to bust his lip or break his nose. Then I did. I turned to jello. I fell and he helped ease me down and once again, I squirted right on him. It took all of my focus to reach back and pull his dick out of me. I had too. Everything was so good but so much. My tolerance wasn’t there so this euphoria and overwhelming whole body sensation is too much to handle at times.

I’m just laying in the mess I made and he’s playing with my hair letting me relax. I don’t know how much more I can take. I asked if he was close because I can feel myself getting noticeably sore. He said we can stop but I was determined so I told him no, I want you to finish like this. I really wanted him to cum inside of me, it turned me on so much but fuck did I pay for it all week. So he says 5 minutes and we’re done regardless if I am or not. I agreed and then we tried it on our sides in a 99 position. He pulled my top leg into my chest and began to push back into me. Oh, my, god… the pressure from that angle makes me quiver. He can push straight up into me with virtually no resistance and it actually felt the best at this point. For me, specifically the rim of my ass and that spot where it curves are hands down the most sensitive. I understand physiology, but there’s always exceptions and I think I’m one of them. My actual entrance is the most sensitive area on my body. That first inch, maybe two, is like my clit, g spot, and every other erogenous are on my body rolled into one. This position is perfect for hitting every aspect of it and it’s just smooth intense sex that we can both participate in. I’m watching him fuck me in one of the mirrors and I’m into it. I begin masturbating and I was having the best sex of my life at this point. On par with our second first time together. He’s kissing my neck and earlobes then whispers in my ear, do you want me deep or shallow. Now I get cocky. I reached back, grabbed his balls and told him as deep as he can which I immediately regretted saying because IT, WENT, DEEP. I think he bruised my heart. Something psychological about seeing myself in the mirror getting fucked, feeling it, but seeing my pussy empty turned me into this fanatic. Like I wanted more and more, but I was still new in his house and didn’t want him to think I was strange. It’s only January and I moved in in October.

So I couldn’t back out from my demand so I put my hand between us and placed my fingers around his cock so it was a handjob and anal at the same time. Boy he liked that. He told me to squeeze him tighter. I was unsure what he meant so I clinched and tightened my grip. Then I felt him. He began beating and throbbing and a sigh of relief and excitement rushed over me. He said he was close and I told to shoot it deep inside of me. Of course I say that with my hand still acting as a barrier. Feels like he’s trying to crush my fist then all of a sudden, I feel him swelling before he bursts. He’s not very loud, but I hear him exhaling deep euphoric breaths on my neck and hair then I feel him exploding inside of me. It came out hard with weight and momentum behind it. The veins in his arms and shoulders implied a lot of relief. He made noises I’ve never heard him make which boosted my confidence through the roof. I was so impressed with myself. I didn’t think he would stop cumming. It just kept beating and I was thinking to myself, this can’t be normal. Then he pulls out and let’s the rest drip out on my hip and asscheek. I looked to see his dick dripping one last drop and I’d be lying if I said I didn’t want it in my mouth. He’s kneeling over me with that flashlight resting on my hip when I told him I can feel it inside of me and how warm it was. I was proud of myself and he looked exhausted. Well, cum began leaking out of me which is hands down the weirdest feeling I’ve ever felt. So Dennis sees me clinch to keep it from getting on our sheets and sticks one of the plugs up my ass to keep the rest in. Thoughtful of him. Shocked and impressed I said, didn’t want me to waste any?

We’re cuddling and kissing when I had to get up. I told him we’re both disgusting and we need to shower. He laughed when he saw the plug was still in. I didn’t want it running down my legs or ending up on the floor. The next few minutes we’re… odd, to say the least. He’s on the bench, I’m standing in front of him and he’s got his fingers in my ass so I can shoot water inside of me for obvious reasons. I had to rest. I knew I was in trouble come tomorrow morning so I sat down next to him and he up and decided to go down on me. I told him, don’t you dare touch my ass, and he just slowly took his time massaging my clit while I came down off the sex high. I did a lot of standing at work on Tuesday and Wednesday. He’s so sweet he went down on me just because I was sore. I said we could have sex but he was adamant about not hurting me so he said he owed me some “free ones” as he puts it. That next morning was rough. Especially getting in my car which is higher up so that leg lift to slide in my front seat was brutal. He was so sweet catering to my every need all week. I didn’t ask for anything, but he catered anyway. I love a calf and scalp massage so I got plenty while my poor ass healed.

So that was my first time doing anal. May have been 20 minutes total, 8 of them of me just laying there catching my breath or recovering from blacking out. Not first anal thing ever, just anal sex and it was more than I ever imagined it would be. The only thing topping that is double penetration with a toy. Wow, just wow. Working both holes in tandem with Dennis is a feeling that can’t be described. I’ll try anyways, but it’s the only thing that feels like that. That’s another story though.

Source: reddit.com/r/gonewildstories/comments/ewun6f/fm_my_first_time_receiving_anal_blissful_but_i