More than Vanilla

I never considered myself gay. Quite the opposite, actually, I was as straight as any guy I'd ever met. I wasn't necessarily opposed to gays either, I just wasn't one. But I dated this girl named Nikki who is absolutely convinced that everyone has some strand of not-straight in them. Maybe you're gay, maybe you're bi, maybe you're into something else I don't know about but is undoubtedly a fetish somewhere. Nikki believes that everyone has something in them that isn't vanilla, and she wanted to help you find it. For your own good of course.

I'm willing to try anything once, a piece of advice I picked up as a kid and have lived by ever since. It's how I came to study foreign languages and cultures, how I came to enjoy such a variety of foods, and how I met Nikki in a random theater production I signed up for just because I'd never been in one before. Nikki got the female lead, I got to be a side character with a few convincing lines if I do say so myself, and a little after the show wrapped up, we started dating.

To stay on topic as much as possible, I won't go into the full politics of Nikki, but to put forth the relevant part: she believed that "normal" was the face people put on to fit in to polite society, and that because "normal" was all anyone sees, the mistake is frequently made that people start to think they are "normal" inside and out. She wanted everyone to embrace their "weird," maybe not out in the open, that's what "normal" is for, but in their own private lives, everyone should find what they were and what they wanted and live like that.

Full disclosure, I do not necessarily think her ideal was wrong, I just think she was a bit aggressive in her pursuit of said ideal. Not that I minded much, like I said, I'm not trying to get into the politics of Nikki, only the relevant part, and the relevant part here is that she brought those ideals to bed. It made for hands down the most varied and enjoyable sex in my life. It also made for some awkward moments where one of us turned out not really be into that, thanks but please let's not do it again.

When Nikki said we might bring another man too bad for a three-way, I was open to the idea. I'm not overly jealous, so if I'm still participating, I see no reason why she can't have some extra fun. I can only be in one place at a time after all. I told her as much and she laughed. Turns out, she had that kind of three-way before. She said we could do that if I wanted, but she more meant the other guy for me.

As I said at the top of this story, I always considered myself straight, so I naturally vetoed the idea. I don't think it counts against my motto, I was reasonably sure I wouldn't enjoy it so I didn't think it mattered. Saves time to just go ahead and skip it. She seemed dissatisfied and wanted to argue the point, but in the end I guess she decided an idea I was so opposed to wouldn't be worth submitting me to. We moved on to other adventures.

Probably about two weeks later, Nikki was giving me a blowjob. She was always very good at that, and by this point, she had my soft spots down pat. But I had had a rough couple of days, trouble at work, I had bombed a test in one class and had another coming up in a class I liked less. My mind was elsewhere and I just wasn't quite getting there. This was, of course frustrating for Nikki because on the one hand, she knew she knew what I liked so if she couldn't get me off something was wrong and on the other hand, blowjobs were not her favorite thing in the world. She did them mostly because I liked them and they could usually be done in a few minutes, unless she was specifically drawing it out.

As I was sitting here, not really fully involved in the delightful things Nikki was doing to me, I felt something new in the same general area she was working. It wasn't much, but it was enough to bring my focus back down there and in almost no time at all we were done. Nikki was happy it was over and I was happy to have gotten what I had. Boys will be boys, and I do not apologize for my own simplicity. A couple days later, I had taken my other test and didn't think I had done so well, and so we wound up in the same situation. Again, Nikki was somehow able to draw my attention to her efforts and we were done in no time all.

I didn't really think about the event at all, and we went back to business as usual. My second test came back better than I thought it would, and everything at work had straightened out. It was a week and a half, maybe two weeks afterwords that I started to feel a little dissatisfied in Nikki's headwork. She was doing what she always did, what I had always enjoyed, but for some reason, I just wanted a little more. I brought it up that I still liked blowjobs, of course, but whatever she had done when I was in my funk might be worth bringing back. She smiled and said she would start incorporating it into the routine.

The next night (I had to work that night, or we would have done it then), Nikki was doing her thing and I was enjoying it with the slightly lowered appreciation I had had for the past few days. Then I felt it, the strange thing she had done that brought me back to the action. It was just the tiniest thing, but it worked. I tried to hold on, to savor whatever it was she was doing. It wasn't until a split second before I finished that I realized what her secret was. As Nikki drank up everything I gave her, I focused on what I thought it was. Sure enough, when she was done and pulled away I felt exactly what I expected to. Nikki had slid a finger into my ass, not all the way, but enough to grab my attention.

I kind of wanted to object, remember I thought I was straight, but I thought better of it. I was secure in my sexuality, I had literally asked her for it, and even if I did like it, so what? I enjoyed it and that's what it was all about. Over the next month or two, she continued with her new trick, occasionally putting her finger in deeper, sometimes drawing her finger in and out or moving it around, and, ever so rarely, even using more than one finger at a time.

Of course, we did have other sex, but those are other stories. Nikki did add fingering my anus to her repertoire outside of blowjobs of course, it wasn't an exclusive thing. The next relevant part of this story comes much later, though. I had been a long while, probably a few months, since Nikki started using her fingers in her special way. One day we were doing a little bit of kinky domination stuff, not really BDSM per se, but I was calling her mistress and she was in control. That was one of her favorite ways of having sex. It was one of mine to, the only thing I liked better was reciprocating.

Nikki had been riding me with my ass slightly elevated so she could reach back and finger it, but her hand was starting to cramp up, something that happened every so often. She apparently got an idea and walked over to her dresser, making a production out of every step. I was tied to the bed, so I wasn't going anywhere. God, she was good at teasing. She made a production of rooting around for, and finding something in her drawer, then of hiding it behind her back and walking back over to me.

She sat back on top of me and slid me back into her. She pulled what was behind her back out and I saw something I rarely ever did, her dildo and lube. I knew she had it, but it usually only came out for her own use when I wasn't around. I wasn't exactly sure why she had it at first, but it dawned on me quick enough. I normally might have protested, but as deep as I was into the roleplay and as hot as I already was, I didn't really care what she did with it, so long as she didn't stop. Sure enough, she lubed up her dildo and reached behind herself with it. I felt a pressure on my anus, then she pushed it in. It slid in more easily then I had expected, but not without difficulty.

It was then that I felt another new sensation. As it turns out, Nikki's fingering was a fun little kink, but she could barely reach my prostate on a good day. Her dildo was much longer and reached all the way to my prostate. I didn't know I could feel anything like that, it was an entirely new sensation. She began riding me hard as she slid her dildo into and out of my as. My breathing picked up and I began to moan in ways I had only ever heard women moan before. Oh, this was a new experience alright, and It was working. It didn't take me long to climax after that, and Nikki incorporated that, too, into the routine.

Again, it was some time before the next thing happened. Nikki had a strap-on harness from a past girlfriend that her dildo fit into, and she pulled it out about a week and a half after she first pulled out the dildo. I vetoed it at first, and I vetoed it again when she tried a week later. Finally, one more week after that, I relented. She slipped the dildo into the harness and pulled it on. She lubed it up and we got into a position that was so familiar but at the same time unsettlingly wrong. She was standing, just off the bed. I was laying face up on the bed, my ass hanging out toward her and my legs up in the air, over her shoulders. Normally, our roles were reversed.

She came up to me, and put the dildo next to my dick as she pulled out the lube to grease it up. This had been the first time such a comparison could be made, but as it turns out, her fake member was slightly thicker and about an inch or so longer than my real one. I might have felt a little emasculated if she wasn't stroking both of them at once. She pulled back to line up, and I felt the by now familiar pressure on my anus. She wrapped her arms around my legs, the way I sometimes did to her in that position, and she pushed. Her dildo slipped right in, and I felt it rub against my prostate. I've heard the prostate be called the "male g-spot" before, and I have to confess, I can see why.

Nikki took a few slow pumps to make sure she would stay in and she had enough lube, and once she was satisfied, she began drilling me. I had wondered what it was like to be plowed as roughly as I liked to plow her, and apparently, she had been keen to inform me of exactly that same thing. She slammed her hips into my butt again and again. She stopped for a split second to turn the dildo's on-board vibrator on, and instead of wrapping her arms back around my legs, she leaned over me and put her arms on either side of me. I reached my arms up and draped them over her neck as she pounded me into the bed, a complete role-reversal of one of my favorite positions, and in a few seconds, what would become my new favorite.

She thrust into me as hard as I ever had into her, but she was starting to run out of energy. Her thrusts would slow down for a couple seconds, then pick back up, and then slow down again. I think she was about to stop and move on to something else when something that had never happened before did.

She was on one of her thrusting bouts, more energetic than the last few, but definitely losing steam when it happened. I came. This wasn't anything new, I came every time we had sex, frequently even multiple times a session. The part that had never happened was that she wasn't touching my cock when it happened. She hadn't touched it for a good few minutes before, when she was lubing up her dildo before sliding it into me. I had cum in her mouth, her ass, even inside her vagina (with a condom on, obviously), and I had done all three of those both without and, in the last few weeks, with her dildo in my ass. But this was the first time I had ever cum with only her dildo on my prostate.

We both kind of just froze there in shock. Because of our position, my cum had shot up her stomach, and coated the underside of her breasts, before dropping down onto me and covering my stomach. We sat there for a second, both just breathing heavily and looking at each other. The dildo quietly buzzed in the background. After almost a minute, she finally reached down and turned of the vibrator, then we both got cleaned up. That had been the most intense orgasm of my life to that point.

Needless to say, I was somewhat more open to her use of the dildo and strap on after that. We did still do all of our other favorites, of course, but my favorite from then on was anytime she fucked me with her dildo. It never crossed my mind that that was bordering on what I or some of my friends might have called "gay" at the time, or at the very least a year before. Nikki and I spent a good long while doing that, and eventually, she again put forth the idea that we could have a three-way, with another guy. She did add that the new guy could be mostly for playing with her, and maybe with me if I was game but not at all if I didn't want to.

Since she put it like that, with him being mostly for her, it wasn't gay (per my definition at the time which I hadn't bothered to update), so I consented. She invited a friend of hers named Tony and we all go along famously, before we took any clothes off. When we did finally take our clothes off, the dial turned to 11 real fast. Tony and I double penetrated Nikki in every conceivable permutation. She pulled her dildo out, and then her strap-on, and fucked one of us while the other fucked her, and we tried all of those combinations. Not all at once mind you, Tony was in the mix for three weeks or so.

Then, as you may have noticed a pattern by now, something new happened. I had Nikki on the bed and was pumping into her like usual, nothing heavy or fancy, just enjoying it. After a little while, sure enough, I came, but I very suddenly realized something. Nikki had been under me, her dildo and harness still in the dresser for the day. And if that was the case, then why did I feel pressure on my prostate? I looked behind me and saw Tony, who, as you may have guessed, had his dick in my ass. Anther man's cock was in my ass. He was, by all accounts, fucking me. Or at least he had been, because as I pulled out of Nikki, he pulled out of me. I saw that the condom he was wearing, like mine, was full of cum. Another man had fucked me, and cum inside me...and it turns out, I didn't mind so much.

It bothered me how much I didn't mind, so I forced myself to make a little scene about it. I made Tony promise not to do that again if I didn't ask for it which I totally would't (not really sure if I believed that last part). Tony still came over after that, the three of us still had sex in various ways, and I pretended to come around a little bit. In reality, Tony's cock was even bigger than Nikki's dildo, and while hers could vibrate, his had a warmth that hers didn't. I denied to myself that I was beginning to crave his dick over Nikki's dildo, but in hindsight, it was pure denial without truth or really even any conviction.

I proved as much that weekend, when we all got drunk. Nikki and I were having sex, missionary style on the bed. Drunk me isn't creative, ok? Tony came around on put his cock right in Nikki's face so she could suck on it. Given the position we were in, it happened to be right in my face to. Being drunk, and half-because I was egging her on and half because they were both egging me on, I helped out a little. That was the first time I had ever willingly taken an actual cock. We all seemed to enjoy the experience at the time, but we all woke up hungover the next morning and apparently I was the only one who remembered that detail. I was ok with keeping it to myself.

The next week, Nikki and I happened to get started before Tony showed up, and I had her up against a wall doing my thing. When Tony walked in, I made a half-hearted apology for having started early and then said something to the effect of "take every piece of ass you can, whenever you can," and then slapped my own ass for emphasis, seeing as Nikki's was up against a wall. Tony took that as an invitation. He walked over to Nikki's drawer and grabbed the lube, stripped, then walked back over to us. I had, by this point, kind of forgotten he was there thanks to Nikki.

And then, right as I thrust into Nikki, Tony thrust into me. Now I had Nikki pinned to the wall, and he had me pinned to her. God was it hot, but I pretended to resist all the same. he repeated my line back to me, slapped my ass for additional emphasis, and we all went back to work. He came in me right before I came in her, and i felt the warmth of his cum pouring into me, since he hadn't put on a condom this time. I did my best to pretend it was Nikki that had made me cum, and I think they both bought it without any difficulty. I bought it at first too, but the more I thought about it, the more I focused on the feeling of Tony's hot cock on my prostate and his warm cum flowing into me than I did on Nikki's now familiar pussy.

I made a compromise with myself. When they were drunk, I mean really drunk, I would encourage (in my own head I used the word "allow") Tony to have a little more fun with me than I otherwise allowed. On nights where I was reasonably sure neither of them would remember in the morning (a calculated risk, I know), I would let Tony fuck my ass sans condom, or sometimes I would help Nikki suck him off. I also let him start fucking me with a condom on certain occasions if our position made it difficult to get to Nikki, or special occasions like his birthday.

I mentioned it was a calculated risk? Well I should have had someone double check my math. Tony and I woke up one morning ahead of Nikki, after a night in which I had been very generous to Tony. Through his pounding hangover, he was smiling at me. I smiled back, at the time not realizing he remembered. Tony was a nice guy to begin with, but he was especially chum that morning before Nikki woke up. After she left to go have a couple bloody marys with a friend, Tony walked up to me.

He said that last night had been fun, and I agreed. He continued saying that Nikki was one hell of a girl, and I said yes, she definitely was. He came up behind me as I was pickup wine glasses. He slid one arm around my waist, reached the other hand down to massage my cock through my pants, and began to grind his own cock against my ass. He said I was one hell of a guy too. I started protest, but I could feel his cock hardening in his pants and my argument turned into something between a moan and a sigh halfway past my lips. I feebly struggled to get away, but his arm around my waist shot up and he wrapped his long fingers around my neck. This man had learned my weak points. I could have said no if I wanted to, and that thought crossed my mind but by that point, I didn't want to.

He undid my pants and slid his hand into my pants, pulling out my cock and stroking it gently. I licked my lips in anticipation. I wanted to stop, but I didn't want him to. He undid his pants and pulled out his own cock. He pulled down my pants and pressed his cock into my ass, like a hot dog in a bun. He began a sort of sawing motion, up and down, rubbing against me. I couldn't pretend the idea wasn't turning me on, especially with my rock hard dick in his hand. He was so close, I could feel his phone vibrate in his pocket. He pulled it out, laughed at a message and sent a quick text back to whoever it was. He tossed his phone on the couch and dragged me into the bed room.

He knew where all of Nikki's toys were by now. Damn her for having so many. Curse her for letting him know where she put them. He grabbed the rope. Thank god she had left the drawer unlocked (I didn't realize that statement wasn't like the others until later). He died me up and began toying with me. He played with my cock, he made me play with his, he used Nikki's toys to harass me, but he didn't actually fuck me. It was torturous, and I thought he was going to make me beg. I was just about ready to when I heard the door open. He called out to whoever it was and told them where we were. A few seconds later, Tony's boyfriend John walked into the bedroom. The biggest shit-eating grins I ever saw crossed their faces and they both looked at me.