[kink][mf]my first satisfying sexual encounter/had my first PiV orgasm with a human sex doll

God, where do I even start? I guess this began about a year ago when I posted on /r/sex about how I had some intimacy issues and stuff like that. Feel free to read about it in my history, but basically, I loved the idea of sex, watched lots of porn, but when it came down to the real thing, I got all flustered and self-conscious and had to stop. Even when masturbating, sometimes I’d start obsessing over stupid details and lose all my sex drive. I’m still pretty much the same, I don’t really seek out sex because it’s just too much to handle for me most of the time, but I did have one encounter that gave me some hope, along with a lifetime of fantasy material…

At some point while I was talking about this issue on Reddit, it was suggested that maybe I should try taking complete and total control of the situation. Basically, find a guy who could act like a sex doll. I liked the idea and so began my search.

Admittedly, it was a tall order. I needed a guy who could handle only being able to cum when I want him to, who had a penis the same size and shape of my dildo, which I had been practicing on, who was basically hairless (not sure why, but I hate body hair), and who would let me do anything I wanted to him without talking or moving, no matter how weird or awkward it might be. I had considered an actual sex doll, but I really wanted to experience a real penis and see what kinds of things I was in to sexually that I might not even know I liked yet.

After a while, it seemed pretty hopeless. I had plenty of interest, but no one who could really deliver on everything I was asking for, there was always some compromise they’d want to make, but I wasn’t about to settle. I wasn’t desperate to get laid, I just wanted to play with a cock on my terms.

After nearly a year, I finally found someone who seemed worth meeting. It turned out Fetlife was the place to go. I found a guy who’s profile literally said that he wanted to be a live sex doll. We texted a little, he told me he had Viagra, and before I knew it, we had plans to meet in at a hotel. I mention the Viagra because it’s something that’s always intrigued me. I like watching porn where the guy is on it, it basically makes him in to like a human dildo, it’s kind of everything I’ve ever wanted. I wouldn’t need to worry about keeping him hard, I had science to do the bulk of the work.

I spent the next few days obsessively grooming myself and watching absurd amounts of porn, literally taking notes on the things I wanted to try. I was nervous to say the least, but I wanted to see where this went and for whatever really, really wanted to play with a cock, so I went through with it.

The deal we worked out before we met was that basically, once we got going, he wasn’t allowed to talk, move, or cum unless I wanted him to. We also made a plan for my arrival. When i was in the elevator of his hotel, I texted him that I was nearly there. The door was slightly cracked open when I got there. I knocked lightly and opened the door, to my delight, laying in the bed, there was a very smooth looking naked man with an erection. Now I was getting excited.

We said hi to each other and that was about it before I started getting undressed. I started to put on a pair of stockings I brought with me, along with a sexy bra/panty set, garter belt, and some heels. I’ve always liked seeing women in lingerie in porn, I always imagined wearing some myself, so I went for it. Now normally, it seems like the women dresses up to entice the guy, but up until now, I’ve always just worn this stuff alone in my room for my own enjoyment, so when I noticed the guy looking at me, I got a little self-conscious. I just wasn’t used to anyone seeing me like that in real life and it wasn’t something I had considered to be a thing I’d want to control, but it was in fact, the first of a few things didn’t see coming. The good thing was that we had established that this could happen and his role was to just go with whatever I felt like I needed to do, no matter how weird/ridiculous it might be. So now I’ve realized I don’t even want this guys eyes open. We make a blindfold from his shirt, and I continue getting my sex clothes on. Easy as that.

Now I’m ready to go, I’d spent the last year imagining this scenario and now it was really happening. I had gone over the fantasy in my head over and over and now that it was real, I kind of froze. I could barely process the situation at first. There was this guy, blindfolded on a bed, with a very hard looking cock, shaved all over, just quietly laying there, all for me. Sounds pretty great right? Well…it was! It was the greatest thing I had ever seen, but for whatever reason, I felt really nervous to get going. I had this awful fear that he’d turn as soon as I touched him and get aggressive or something. I felt myself spiraling and almost called it off. Then I decided that instead of bailing, or trying to stuff this fear down, like I may have in the past, I would just say something, after all, we agreed in the beginning that he’d do anything he could to make me comfortable. So I had to tie him up…

Now, I’d never let a stranger tie me up in a hotel room, but this guy was very sweet and probably too trusting for his own good, so he gladly let me turn the sheets into restraints for his arms and legs. I figured once I got going, I might untie him, but this was looking pretty great for now. His arms were tied to each side of the head board and I had his feet bound and then tied to a leg of the bed. He looked oddly like Jesus on the cross, but with a fantastic erection. I’m so sorry, Mom.

Now I was finally ready to play. Dressed in my sexiest (and only) lingerie set and actually feeling excited instead of nervous. I started by straddling his legs down by his knees. Just feeling his legs against my crotch was getting me worked up. I’ve never really been on top of a guy before, so this was big for me. I sat there for a second, taking in all these sensations, then I reached out and grabbed his cock. It was way more fun than I expected. I loved how soft it felt while being so hard. I loved how smooth his balls were and how they’d retract when I touched him in the right spot. I didn’t jerk him off or anything in the beginning, I just held his cock in my hand and observed how it looked, watching it convulse sometimes, as if he was cumming, but nothing was coming out. Then I tried teasing it. I brushed my fingers along his shaft, wet my hand with spit and rubbed the head of his dick with it, and I had heard that if you rubbed the bit of skin just under the head of the penis (the frenulum), you could make a guy cum, so I started concentrating on that.

I held the base of his cock with one hand, wet my fingers, and squeezed his frenulum (such a sexy word, right?) He seemed to enjoy it, I could see him breathing harder and even though i didn’t think it was possible,I swear his dick got even harder. I was curious to see if he’d cum, but I wanted that to happen in a different way, so I just stopped without warning.

When I did, I could see his cock convulsing again, like he was cumming. I just sat and watched him twitch. I’m sure he wanted to me keep going, and I would, just not then. I decided to slow down and make sure his first orgasm was exactly on my terms. I went back to lightly brushing his cock and balls with my fingers, I rubbed all around his hips and stomach and just tried to drive him crazy. At this point, I was getting turned on, and I’m pretty certain it was the whole torture/delayed orgasm thing doing it for me. I had never felt so in control and I loved it.

Despite not letting him cum at that moment, I was still eager to see it happen, I had never seen anyone cum in real life, but I had a laundry list of things I wanted to do with this guy’s cock, so it just wasn’t going to happen just yet. He assured me he could cum multiple times, but I honestly wasn’t sure I believed him and didn’t want to get my hopes up, so I had to keep teasing him…

Now I had never touched a dick until now, I had sex once in the past and it was short and there was no foreplay, I hardly even caught a glimpse of it, so this was huge for me. I know that dicks are plentiful and all that, but not for me, I can’t just hook up and have normal sex, I have all kinds of weird wants and needs and I get so anxious it just doesn’t seem worth it. But this was actually going well! One thing that always terrified me was giving oral. It seemed like so many thing could go wrong and in the end, if you do it right, you get a mouth or face full of semen, which I wasn’t sure if I could handle. I loved watching guys cum on womens’ faces in porn, it was actually one of the first categories, i guess you could say, that I got interested in when I discovered internet porn. Regardless, I always thought I’d puke or something horrible like that, if it were me.

That being said, I was very turned on by now. I had the urge to hop on top of that cock, but I wanted to save that for later, so I decided to try oral. I was still a little scared of this dick on some level, so i got a flavored condom that I had bought a pack of for this exact situation. Once he was wrapped up, I started by just touching it with the tip of my tongue. I doubt this was sexy for him at all, but it was what I needed to do. I just touched different parts with my tongue and watched his reaction. Then I actually started licking. First with the tip of my tongue, then eventually with the whole thing, like I was eating ice cream or something. It took me a little while to get the courage to lick the head of his cock, but I went for it, I licked him from his balls up to his frenulum again, and I took the whole head in my mouth. I just kind of left it there, closed my eyes, and sucked on it gently, rubbing his frenulum through the condom with my tongue. I must have done this for two or three minutes. I didn’t really move, I kind of got caught up in the moment and didn’t want to ever stop. I just held his dick and sucked it like a snake wound. I had no idea if it was doing anything for him, but for once, I didn’t really care one way or another. Covered or not, I had a real fucking cock inside my mouth, this was something I never thought would happen. I have all kinds of anxiety and social issues, I really never expected to have sex. At the most, I expected bad sex with a guy I didn’t really like. Or maybe I’d end up a lesbian, I have no idea, maybe I still will, but I really never thought i’d be sucking on a stranger’s cock in a hotel room wearing sexy lingerie, that is for sure.

So naturally, at one point, I just stopped abruptly. I kind of lose interest quickly in most aspects of my life, and apparently it was no different when it came to sex. Mostly, I didn’t want him to cum in the condom, I wanted to see it happen, so at that point, I told him I wanted to see him cum. I took off his condom, got the lube, poured some on my hand and grabbed his cock again. I actually got chills when I realized how good a lubed up cock feels without a condom on. I’ve used lube on dildos and on my hand when I masturbate sometimes, but this was next level. It glistened beautifully in the shitty hotel lights and at this point, pre-cum was dripping out faster than I ever thought possible, if I didn’t know better, I would have thought it was the real thing.

Not really having any idea how to give a hand job, I just went for it based on what I’ve seen online. I went really slow and used one hand on his balls. Within maybe 10 or 20 seconds, he starts convulsing again and a bit of cum start dripping down my hand. I was a little disappointed because I was hoping for a geyser type situation and I thought that was it, but I was wrong. A second later, a huge blast of cum shoots from his cock, then another, and another and it basically just kept coming. I would guess the first blast went 3 or 4 feet up, I got a bit on my arm and my hand was a mess, but it was the hottest thing I’d ever seen. Now that we broke the ice, I was ready for so much more, and I hoped he was as well.

I untied him so he could go to the bathroom and clean up, once he got back, I did the same. When I got done, he was back on the bed, dick back to being hard. He did say the Viagra would definitely keep him going for a couple hours, but I was still impressed with it. Another thing I loved was how he just went right back to what we were doing. He wasn’t trying to cum and go, this guy was in it for the long haul. I also was still totally still and silent. I was able to just go about my business as this guy just waited for me to come back and touch him. I felt powerful for the first time ever. This guy was my bitch and he loved it. I loved it too. I considered not tying him up again, but honestly besides being a way to make me feel more comfortable, I turned out it was a huge turn on. I tied him up and blindfolded him again, this time a little tighter.

The next step in my plan was to actually fuck this crazy thing. Or at the least, get it inside me and see what that was all about. However I couldn’t stop thinking about what the blowjob would have been like without that condom. Now, the guy said he was clean, but I never believe anyone, so I still had him use that condom, normally I’d stick to my guns, but god dammit this cock was just looking so good to me, I wanted to feel it in my mouth. So I tried something new. Now, I didn’t plan on having this guy eat me out, it wasn’t even in the plan to get close to that, but I was really in to it, so i sat on his face in my panties. I pressed my crotch up to his chin and told him not to do anything but breathe deeply. I sat there and felt the warmth of his breath on my pussy, through my sheer panties. It was strange having my ass in someone’s face like that, but could see the appeal. It felt raunchy and wrong and kind of amazing, so amazing that I pulled my panties to the side and put my bare pussy on his mouth. Like a good sex doll, he didn’t start doing anything until I told him just to stick his tongue out

So he does that and I start rubbing my clit on it, which was new for me and very enjoyable. So much so I decided I wanted to turn around and do it properly. So now I’m riding this guy’s face, pulling his head up closer as I grind my pussy harder and harder on him. It reminded me a lot of the many pillows I’ve humped in my day, but it was a dude’s head…I didn’t cum, but this was by far the raunchiest thing I had ever done, I felt like a slut, and I loved it.

So now I really want that cock…I want it inside me, but since this was probably the only night I was going to be with this guy, I wanted to really make it count. I felt like I missed out by having that condom on during the pseudo-blowjob, so I went for round two. Since I was starting to kind of feel weird about my ass being in this dudes face for so long, I decided that was enough oral on me and it was his turn. I got down between his legs again and grabbed the cock. I really wanted to feel it in my mouth without a condom, but something was stopping me. It really went against everything I’ve learned about sex with strangers, but I did just get done rubbing my unprotected pussy all over his mouth, so I was torn.

At this point, the old me might have just done it anyway, but this was new Anna, and new Anna tells her sex slaves what’s on her mind. So I told him what was up. I wanted to suck that cock, but bare cocks are scary in a way, and I wasn’t sure what I wanted to do. I untied him and we talked it out. After we chatted and got a little stoned, we came up with a very confusing solution, one I can’t even explain how we arrived on, and really doesn’t address the core issue, but it’s what happened…

Before I changed in to my sex clothes, I had on some jeans and this black top with a lace trim on the neckline that really showed off my cleavage. It was literally the one “sexy” thing I owned that wasn’t lingerie. Anyway, since he was kind of a smaller guy, he fit in to my jeans and top. For whatever reason, we also decided his whole head needed to be covered. So now I have this guy, again tied up to my bed, head totally covered in pillows, wearing my clothes, with his STILL hard cock coming out the fly of the jeans. I actually really liked it, the jeans were tight and the fly was so small, his balls couldn’t get out unless I unbuttoned them, but I didn’t want to, so just his cock was out. Without his balls in the picture, it looked more like a dildo than a real cock and since he was now in women’s clothes, MY clothes, he barely even seemed like an actual guy at all. It was like I made a sex doll out of my clothes and pillows and shit (which I may have done countless times) and somehow attached a real cock to it. Basically it was all I ever wanted.

Having no idea what fetish this fell under, I was ready for this. I got down between his legs yet again, grabbed his cock and licked it from his balls up to his frenulum again, but this time when I took the head in, I actually bobbed up and down on it. I had been practicing this on my own for years now, and besides his cock feeling much better in my mouth, it was pretty much the same. I was able to get it pretty deep in my throat, nothing too impressive, but it was more than I ever thought I’d get. I even gagged a little and drooled like they do in the extra nasty porn…Again, I felt like a real slut and I loved it.

Now, I still didn’t want to get a load in my mouth, maybe someday, but not that day. I told him not to cum in my mouth and to yell if he was going to. He assured me he could hold it, so I decided to step it up a notch. I untied his legs and had him roll on his side a bit and I got on mine, facing him. Then I had him slowly fuck my mouth. I didn’t let him go more than an inch or two in at first, I was still scared of giving head, especially with him fucking my mouth, but I’ve spent so many hours watching women get their faces fucked and for whatever reason, that looked fun as hell, so I got as close as I could. The key was to just keep him predictable. Knowing he wasn’t going to suddenly hold his cock down my throat or anything was a good feeling. I just had him slowly rock his hips at a steady rhythm as I closed my eyes and took his cock in my mouth for a while.

At one point, as I was blissfully being gently face-fucked, another idea came to me as I started rubbing my nipples. I remembered that my tits are giant and apparently good for fucking. I’ve had guys online ask me about tit fucking in the past and it always seemed like a good time for everyone. I took some lube and rubbed it on his dick, got closer to him and guided him between my tits. I just held them together and let him fuck them. I wasn’t scared of this as much, so out of curiosity, I told him to do it hard. He really started giving it to me, if it was my mouth, I would have gagged and died, but this felt kind of great. It made me wonder what getting fucked like that would be like…

Maybe it was the weed, maybe I was just insanely horney, I don’t really know, but as he was fucking my tits, i managed to get my mouth down enough to lick his cock. When he first hit my tongue, he pulled back, thinking he’d gone too hard (bless his heart), but I said to keep going. It really worked well because my tits created a barrier that only let his cock in an inch or so. He could fuck them and my mouth all at once and I wouldn’t worry about suffocating on his cock. I loved it so much that told him I wanted to taste cum. He started to go a little harder, I assume he was holding back and was now just going for it. I just stayed there holding my tits together, letting his cock dart in and out of my mouth, tasting his pre-cum, so excited for him to erupt in my face, not worried about anything, it was bliss. After I’m not sure how long, he started to cum. First it was between my tits and then I took his cock in my mouth. I felt a couple more blasts hit my tongue. It didn’t taste as bad as I expected, so I swallowed. When I pulled back, his dick was still convulsing. I squeezed it from the bottom up, like toothpaste, and watched the last few drops come out. I licked the head of his cock and tried to suck up anything that was left. I couldn’t believe how much I loved it. Again, I felt like such a fucking slut. Cum between my tits and on my face and now, inside me. I fucking loved it.

So now it was finally time. I got everything I wanted besides one thing. Even though I did feel pretty comfortable with this guy now, I still needed him in my clothes and I had to still have his arms tied up. It made no sense at all, I have no idea how I’ll have a normal sex life if this is how I have to do it, but whatever, today wasn’t about that, it was about having the experience one way or another. Now, like I said, I’ve spent a lot of time humping pillows and attaching dildos to things so I can ride them, but I still had no confidence in my abilities to ride a read dick. I actually almost just asked him to fuck me, but I had always imagined being on top for this, at least at first. I decided my panties had to come off, so naturally I put them on him over my jeans, he was like a freaky Quailman. I loved it, but it wasn’t quite right, he needed a bra. I only had one because I wore my sexy one over there, so I took it off and put it on him. Now I basically had a crossdresser lookalike in my bed to have my way with. I never knew it was my thing, but apparently it was. Something about seeing him with my clothes and lingerie sloppily put on him was turning me on like crazy. It made no fucking sense, but I. was ready. to fuck.

I put a condom on him, even though my pussy was dripping already, i generously lubed us both up. I straddled him and very slowly put his cock inside me. Once it was in, I was able to sit down all the way and just feel it. It was familiar in that i’ve sat on dildos before, but this was a real live cock inside me! One that shoots babies! There was a time where I was pretty sure I’d never have a real dick inside me, I honestly still don’t know how I feel about men. I really might be a lesbian, I did have to basically dress him up like a girl to get off, but whatever, I didn’t care. I started to really ride him, rocking my hips like I’ve watched women do for years, I wasn’t sure if it would work, but I could really feel him sliding in and out of me. I went slow and really tried to take in the moment and feel this cock, like really feel it. I pressed down hard, getting it as deep as it would go, then i’d slide forward slowly until it was almost out, and I’d go back in again. I was shaking, I could feel an orgasm forming. It was still far off, but I was getting there. At this point, I had a thought that I never thought I’d have…I really wanted to get fucked.

I told him I wanted him behind me. I still had no desire to look at his face so doggy style seemed perfect. I untied him and he asked if I wanted him to keep wearing my clothes, I told him just keep the panties on. He got undressed as I got on my hands and knees and then he got in back of me. I had him go really slow at first and had him hold his cock inside me kind of like I was doing when I was on top. Then I told him to go for it, I wanted him to fuck me hard until I came. He grabbed my hips and did exactly that. He fucked me for what must have been 10 minutes straight. I remember noticing that two songs had played in their entirety, which had to have been at least 7 or 8 minutes of constant fucking. Then he said he was getting winded and wanted to change positions. I still wanted to cum and I still wanted him to do the fucking, so I ended up getting on top. I covered his face again, not sure why I couldn’t stand it, it wasn’t a bad face, but I just didn’t want any part of it, so with his head buried under a pillow, i leaned forward and just let him fuck me as hard as he could from underneath me. It seemed like he could go even faster like this, it was exactly what I needed. When I’m alone, I tend to finish myself off by going super fast, and this felt a lot like that. He kept at it for another song or so until it finally started to happen. I knew I was going to cum, but I had no idea it would be so intense. Wave after wave hit me like…well like a wave. Lots of them. I could barely talk and since he didn’t cum yet, he was still jackhammering away as I started to get dizzy from cumming so hard. He finally stopped. I asked if he came and he said he hadn’t, probably because he already came twice. I was fine with that.

I got off him and laid on my back to catch my breath. Still twitching, still feeling that orgasm. I was pretty sure I had enough. I was thinking about telling him I was going to go, but when I looked over, he was on his back, head covered, wearing my panties, cock still hard. I couldn’t resist one more.

I didn’t know what I wanted to do since I didn’t really have a plan at this point. I just knew I needed more cock. I figured I’d get on top and try to make him cum. If I could get on top of a guy and fuck him until he came, I felt like that would boost my confidence a bit. I did want to try reverse cowgirl. I remember seeing an episode of “Sex Files” as a teen that said it was the most pleasurable position for the woman. I had no idea if it was true, but I had to see. Plus, I loved the idea of having the guy’s balls in front of you to play with…

So I straddle him and guide his dick inside me. I sit down firmly and try to get his balls to touch my pussy. It was just something I wanted to see…When I got there, I started rubbing them. They were soaking wet with lube and pussy juice and just felt so great. I rubbed my clit and his balls all in one motion. It felt so good I forgot about fucking him for a while. I just looked down at my pussy and his balls, rubbing them all over, pushing down on him and taking his cock as far as it would go. I was in heaven. I could feel another orgasm off in the distance and at that moment, I said something I didn’t expect to say, “put your finger in my ass.”

I like to play with my ass from time to time, so I felt like I could handle a finger. I had him lube me up. The feeling of the cold lube on my asshole really turned me on, this was really happening. I leaned forward as far as I could and feel his finger touch me. I relaxed and let it slide in. He only went in a bit at first until I told him to go in all the way. He pushed his finger in as I pushed my ass towards his hand. “Let me fuck it” I said. I then started humping his cock and his finger at the same time. This was amazing! I told him to add another finger, this brought it to a whole new level. Once he was in with two fingers, he pressed down on some kind of magic spot that I could feel in my pussy, and I felt like I was going to cum. I pressed his hand in harder as I kept fucking him. I had one hand on my clit, a dick in my pussy, and two fingers in my ass, this was nothing I’d ever felt before, I wanted to cum, but I was getting a little sore and my legs were cramping, it was taking me out of it, so I just went for it and asked him to fuck my ass.

I got off him and got on my stomach. I wanted him to fuck me in the prone position, as again I heard it was the most pleasurable ways to take a dick in the ass, and I like to test out the things I hear. I had him lube me up yet again and as he did that, I went back to rubbing my clit. I could hear him stroking his cock with lube as he rubbed my asshole. I wasn’t scared at all, I was 90% of the way to an insane orgasm and I wanted that cock in my ass more than anything.

I hear him put the cap on the lube and he gets a little closer to me. Then I feel the head of his cock on my asshole. I relax my ass and when I do, his cock slides in. No pain, just absolute pleasure. He pushes down on me hard, like I was doing to him all night. Then he starts fucking me. At first he didn’t pull out to much, he’d just bounce on my ass. It felt fantastic. Usually when I do this on my own, I don’t really fuck my ass, just put things in it, so this was perfect. As I felt myself about to cum, I told him to fuck me hard. He pulled way out and slammed his cock back in me with quite a bit of force. He’d stay inside me for a second or two and do it again. It felt great, but I needed it faster to cum. I tell him to fuck me faster and naturally he does so. “Can I cum?” he asks. I tell him yes and around then is when I came. I lost track of all time and space at this moment. I had never came from anal before and it was intense. I swear I blacked out for a bit, I don’t make much noise when I cum, so I don’t know if he knew I was cumming. He kept fucking me faster and faster, even if i wanted him to stop, I could barely talk. I was shaking and twitching as I came for what felt like a lifetime. I’m not sure when he came, I don’t even remember him pulling out. I just basically came to after a while after laying on my stomach, twitching, trying to catch my breath.

By now I was exhausted. I assumed he was as well. We got cleaned up and dressed, hugged, and called it a day.

I went home and spent the night masturbating in the tub to the memory of it. I may never have sex again, or maybe just not with a guy. I really have no idea. I do know however, that I can take it in the ass like a champ. Thanks dildos, thanks internet, never could have done it without you.

Source: reddit.com/r/gonewildstories/comments/8nlqta/kinkmfmy_first_satisfying_sexual_encounterhad_my