The Relationship That Made Sex Fun [MF]

So this is about my college boyfriend. When chatting with some people on here he ends up coming up a lot when they ask what I’ve done or what I’m open to. After all, when it comes to anything other than vanilla sex it all started with Alex. So I figured I’d just tell the story.

Alex and I met my junior year. Cute. Blond. Boyish good looks. He was in one of my last prereqs I had to take. He was a year younger. We ended up talking, eventually he asks me out.

The date was lots of fun. He’s a funny, charming kind of guy who knows too well that he’s funny and charming. But what I’ll always remember as being distinct was how nonchalantly he just kinda drops that he’s bi in the conversation. Just talks about a guy he used to date as a side reference to the story. I don’t know how interesting that is nowadays, but even just a few years ago it was surprising to me. Anyway, the date continues. It was great. Total gentleman about everything. Kiss on the cheek at the end. The whole thing. We make plans for another.

The next date ends with us fucking. And I mean, wow. First off, he was gorgeous. Fit. Abs. A little blond body hair over everything. A mouth that was fun to kiss and a tongue he really knew how to use – from my nipples to my clit. And that cock. First off, it was uncut and I had never seen one before. And I fell in love. It was so much more fun to play with. To suck on. To tease. A dick wasn’t just a stick anymore, but had moving parts. Size wise there wasn’t anything unusual about it. But it more than did the job. It was awesome.

So they next time we’re getting naked I’m expecting more of the same. But instead of fucking me after he goes down on me, he fairly dramatically pushes my legs back, exposes my ass and his tongue travels down to my asshole. And I was *shocked*. I was not *this* kind of girl. Ever. But Alex seemed to take my gasp for approval and seriously dived in. He was, for all intents and purposes, making out with my asshole. And before I could really object, I realized how good it felt. I mean, it’s a weird satisfying feeling. But in a good way. So I let him keep going. And before long it’s not just a tongue. It’s a finger. And again, Im shocked. I kinda like it. I don’t stop him. So when he finally asks me if I’m ready, and I know he means he wants to fuck me in the ass, I surprise myself by saying yes.

I’m not going to lie, it burned. I felt very full at first. I kinda regretted it. But my first time losing my virginity wasn’t all that great either, so I told myself to bear with it for a bit. I think he could tell I was uncomfortable because he kept telling me to just relax, that he was going to go slow and that I would loosen up. He promised. And he was right. And each slow, gentle pump of his dick stopped feeling like a hot burning poker and instead started feeling good. Satisfying is a really good word for anal. When it’s good, it’s satisfying. By the end, he’s fingering my pussy while fucking me in the ass and I was loving it. Orgasms all around.

So a few weeks later, we’re having sex at his place and I’m blowing him. I’m enjoying it, I’m fairly certain he’s enjoying it, but at some point he pulls my head off his dick. And I look at him confused as he grabs both his legs and pulls them toward him and suddenly his asshole is looking at me. I’m not going to lie, I had a feeling this was coming. A guy probably doesn’t make out with your butt without eventually expecting it back in turn. So I had been psyching myself up for this for days. I was ready.

I very *very* tentatively put my tongue on his butthole. I don’t know what I was expecting, there was some light fuzz around it, but it was clean otherwise. It had a taste, but it’s not like it tasted bad. It was fine. It wasn’t scary. So I did it again. And again. And before long I’m getting enthusiastic about it and he’s enjoying himself… and he stops me. Again.

Alex hops up and I ask him what he’s doing. And he starts telling me that he wants to try something. And to not freak out. All the while he’s digging into the back of his closet. And that’s when he pulls it out. At first it just looks like a mess of leather straps. I very quickly find out that it’s a strap on harness.

Yep. I can’t believe what I’m hearing or seeing. I ask him if he’s insane. He laughs and says maybe. Tells me we don’t have to if I don’t want to but he thought it’d be fun to switch things up. I don’t know how to respond. I’m honestly in shock. Somehow he gets me into the thing and I’m looking down seeing this black dildo sticking out between my legs. I feel absurd.

Alex is grabbing lube and feeling up his own ass before laying back down on the bed. He’s saying let’s just give it a try. We can stop if I don’t like it. I laugh at that. I walk over, this weird thing swinging a bit in front of me. He lubes it up a bit before laying on his back by the edge of the bed before asking, “Ready?”

So I saddle up to him and slowly point this thing at his hole. I remember feeling like a bobble head, constantly looking up and down from his face to the big event. As i slowly pushed it in, I remember him grimacing for a moment that scared me, but just a second later as it went deeper Alex sighed with relief. And I thought that definitely wasn’t my reaction the first time he was in my ass. He has definitely had things in him before.

In fact, Alex LOVED this thing in his ass. Almost immediately he has me pounding away at him without any sort of adjustment time. He’s moaning like crazy and his dick is drooling and I’m very quickly finding out that being the guy in sex is a lot more work than I thought. Like, thrusting takes work. It’s really tiring. But the way Alex was reacting I wanted to keep with it. I wanted him to enjoy himself and god was he.

At some point his stomach is basically soaked in precum and I wipe my hand in it and grab his cock. His face bulged and he quickly told me that if I keep doing that he was going to cum. So obviously I start jerking him even faster. My coordination gets kinda off so my thrusting kinda looses its energy, but the dildo is still in him and I’m jerking him off and then he just explodes. A freakin’ cum fountain. Past his head at first, but then he hits his face repeatedly and then all over his chest.

And we’re kinda just sitting there for a moment and then we just crack up laughing.

And that was my first time pegging a guy.

Alex and I dated for two years, until I graduated basically. There’s one more interesting addition he brought into my sex history, i might tell that in another post.

Source: reddit.com/r/gonewildstories/comments/5g9ol3/the_relationship_that_made_sex_fun_mf