A Big Stretch

Because Sveta will soon be having her first anal insertion (maybe tomorrow, if she doesn't have too much homework) I was thinking about my first time with anal, and I realized that didn't really help. Because my brother was much younger, and his cock (sorry Mike) was pretty small, not as large as James' will be. Not only that, but we'd been fucking for a long time, whereas James and Sveta only recently started (well, recently enough).

So I've been trying to remember the first time I had a larger cock from a guy I didn't know as well in my ass. It's not quite the same, because I had done it before, but still, up until that point, everything in my butt had been pretty small.

I wish I could say that I went out and found a perfect stranger to fuck me in the ass right after my first time with Mike, but I'd be lying. For all that I enjoyed my first time, it wasn't the most comfortable thing at first, and I knew that a larger cock would be even less comfortable. Sheri told me I should find a big cock right away, but I told her a little snarkily that she hadn't, that Mom and Dad had to find one for her. I think that hurt her feelings. I should have been nicer, but it was true. She had a big cock mostly because Mom and Dad set it up with Fred.

So it took me a while. I let Mike fuck my ass all the time, but it took me a while to want to move beyond that comfort zone. Because it was really fun with Mike, not stressful or painful or anything. But eventually I did want to try something larger. I could have used a dildo or a plug or something like that, but I wanted to try a larger cock. At this point, I was hungry for older men anyway; sex with teenagers can be fun, but I really do enjoy a more experienced man, especially one who is grateful to be allowed to fuck a teen (as I was a teen at that point).

But I wasn't about to ask Mom and Dad to set me up. Dad did set me up a few times with friends of his (not that it was like he was pimping me out or anything, just that he knew I wanted a fuck and he knew these guys would be nice to me) but I didn't want to ask for this because I wanted to do something better than Sheri. Sure, I was a little jealous.

So I tried to meet older men. And when I was that young, that was pretty hard. Everyone was always so nervous about it. Which is why having Dad set me up with guys worked out so well. But anyway, I tried lots of things. I tried babysitting, and let me tell you that while some guys are really harassing, they never actually want to do anything. I know it happens, but all the guys I tried to come on to just wanted to flirt with me. Such teases. Really pissed me off. I tried to seduce guys at the pool. That worked about as well as you might expect. I did get to have a quickie with another guy a few years older than I was because I was trying to come on to his father and he thought I was coming on to him. So I said, what the hell, and fucked him. I don't remember where. I do remember he came buckets, I mean it was unreal. He must have been incredibly hard up. But it didn't get me any closer to having sex with his father, and I couldn't very well just ask him to make that clear to his dad when he left.

It seems really silly now, because frankly, there's absolutely no guarantee that an older guy is going to have a big cock anyway. I could have seduced some guy who was hung like a baby. I did try to look at bulges, but it's a lousy way to pick a large cock.

It took me a long time before I had to admit that I was licked and ask Sheri if she knew anyone who had a big cock and wanted to fuck me in the ass. She, of course, had totally forgotten all about it by that point. She was great, said she'd get me a guy as soon as possible. That's why I love Sheri: she doesn't hold a grudge. Me, I was worried about it, and she had totally forgotten our exchange.

Obviously Sheri had more luck with older guys, although she still wasn't able to get adults. But she could get guys even in college (she liked to pretend she was a coed, and she could pull it off) so she set up a sort of double date. We went to a concert with two college guys, probably freshmen. Then afterward she and her guy split off and left me and mine alone. I remember his name was Craig, although everyone seemed to call him Craigie. I didn't want to do that, and he didn't seem to like being called that.

A huge stud he wasn't. I mean, how many huge studs go out with girls who might possibly be freshmen in high school when they're in college? I wasn't a freshman in high school, but the topic never came up. I don't think he was expecting anything to happen. The fact that I was kind of nervous probably didn't help either. He took me back to his dorm room, which was something of a mess.

We were trying to make small talk, and I was starting to wonder whether it was a good idea. But I did think of Sheri, who was probably even then sucking her guy off. So I asked Craig if he wanted to make out. I was such a smooth operator: "Hey college guy, do you want to fool around?" I cringe thinking of it. He seemed pretty enthusiastic about that, so we made out on his bed. I don't think he was any more smooth than I was. Certainly his technique left a lot to be desired.

Frankly, looking back on it now, I'm not sure what the hell I was thinking, or what Sheri was thinking. I mean, this guy had probably only not been a virgin for a year or so, maybe. And he certainly wasn't an anal expert. Why was this a good idea? I don't know. I do know that I started to get pretty hot and heavy and although I still harbored some doubts in the back of my mind, I wanted a fuck, right then, even if we never made it to anal.

When I asked him if he had any condoms, his eyebrows hit the ceiling. But he tried to act cool, said there were some in the dorm (we always kept the condom supply in our kitchen when I was in college, but I don't know where these were) and he would get them. I told him I had one in my purse. Actually, I had a lot in my purse; be prepared, kids. I also had lube in my purse too, mostly in case I was somewhere with Mike and he wanted anal.

He was hard as a rock but he seemed bound and determined to make me suck him. The amusing thing was he was so much older than I was and yet I wasn't much shorter than him. He was short, I was tall. Anyway, he sat on the bed and unzipped his fly, and his cock sprang out. It was definitely bigger than Mike's, although it certainly won't make the list of big cocks in my little book. But it was an ideal cock to graduate to bigger cocks.

He lasted in my mouth about three seconds before he almost screamed that he was going to cum and grabbed my head. Guys, why do you do this? You've watched too many pornos. Gals do not generally like it without warning. But he loved spraying cum all over my face; some made it into my mouth but a lot of it got all over me. He tossed me a dirty shirt from his floor to clean up with. Classy. I shoved it away and cleaned up with my fingers and tongue, which he thought was dead sexy.

I tried to get him back to life with hands and mouth, and for a few minutes I was afraid that was it, but he did come back up after a while. Then I slipped the condom on him and got up and carefully took my clothes off. He was shocked at how young my body looked, I think, maybe having a few second thoughts. But my tits caught his attention, and then when I laid back on his bed and spread my legs and toyed with my pink pussy, it was like fish in a barrel.

He didn't have any trouble fucking, which is why I say he probably had some practice. It wasn't even bad, just not terrific. He was naked, I was naked, we kissed, he fucked me in my favorite position, I wrapped my legs around his back, and basically I decided not to worry about anal. I managed a small O before he came, and so I felt fairly satisfied with the evening (especially since I knew I could just go home and get Mike to service me properly if I wanted a cock, or Sheri and Mari if I wanted that).

We were lying wrapped in one another when the door opened and Sheri and her date walked in on us lying in bed naked and sweaty. Sheri grinned and nudged her date, who grinned back and said something to the effect that her sister must really be horny if Craigie got her into bed this fast. I guess they were expecting to come back and find us still talking. Well, maybe not Sheri.

Craig was mortified, jumped up, grabbed things to cover himself, turned beet-red. Sheri's date told him to get some clothes on and go for a walk. I was all set to do the same, because I realized the two guys were roommates and figured that Sheri and her date would want to room for a while. But she gave me a little shake of her head, so I stayed put. Craig practically ran out. Sheri scolded her date, whose name was Javi (short for Javier I assume, but no one ever called him that), for being so mean to Craig. Then she turned to me and motioned me to scoot over so she could sit down on the bed too.

It turned out that her plan all along had been for Javi to fuck me in the ass. She had fucked him before, knew he was good, had a nice cock, all that. She just had to ask him, which was why they split off. And by ask him, I mean that she had to warm him up first. I don't think she told him who I was, any more than she told Craig, but Javi didn't seem to mind at all that I looked so young.

He was the first Hispanic guy I'd even fucked. Once Sheri explained, she got up, and Javi pulled his shirt off. Sheri has very nice taste in guys; he was built. And when he dropped his pants and displayed his cock, I was a little nervous because he was built large. Much larger than Craig's had been. Sheri laughed and said that she bet I wished I had waited. I said that it didn't matter; I wanted more.

Javi didn't waste any time. "Roll over," he said with just a trace of an accent. I don't know, he might have been from Brooklyn for generations for all I know. It just was a trace. His skin was tan, his muscles taut; thinking about him is making me salivate a little. But I rolled over.

He spent some time feeling me up with lubed-up fingers, diving into my snatch and rubbing up and down my lips. It made me wet, very wet in fact. If he had been trying, he could easily have made me cum just doing that. But he was just working on me.

When he pressed the first finger into my anus I sighed with appreciation. The second finger made me a little anxious. The third, shortly thereafter, made me cum, but it was difficult to really enjoy it because I was stretched so far. He didn't do anything but keep the fingers there for a while, then he started fucking them in and out slowly, then pulling them out and pushing then back in. It felt wonderful but also kind of painful. It was like taking a monster shit, really, except it just kept going. You know how after you drop a deuce, so to speak, there's that moment when it's out and you relax? Well, there wasn't that moment.

But eventually, just like with my first time, I realized that the fact that the sensation didn't stop was actually very enjoyable. And it was then that he got up and moved to stick his cock in my ass. And he wasn't wearing a condom. My sister's poor influence. I didn't realized that, of course; I was busy working on the sensations.

The cock wasn't as thick as the fingers, but it went deeper, much deeper, and that was hard too. He went in faster than I think I will with Sveta, or James should when it's his turn. When he bottomed out I cried a little. He did leave it there and let me get used to being so full, but then he pulled out and pushed in again. It's the depth that gets you, not the stretching. The depth made it very hard. I could have dealt with him fucking my ass with his fingers, but when he went deep, it hurt, I won't lie. I've since not only gotten used to being taken deep like that, but I also enjoy the sensations, but back then, it was painful.

In the end it didn't matter. He fucked me anyway, and reached up with his hands and diddled my clit until I was cumming even with the strain of it. He wasn't a marathon, not in my tight ass, but he lasted long enough to make me appreciate not having a cock in my ass, then he came inside me. I couldn't feel that, but he stopped thrusting so quickly, grunted, and the sensation was like he was deflating inside me. He wasn't really, but any small change made it easier.

He slipped out of my ass and made to go around and feed me his cock, but Sheri intercepted him and cleaned him off. She likes doing that. Me, I'll do it, but at that point, I might have freaked out. When he was out of me I still felt like there was something inside me, and when I moved, it wasn't entirely pleasant. Sheri finished cleaning and said that we had to get going, so I awkwardly put my clothes back on and we left, with him sitting naked in a chair watching us go.

I can't say that it was the greatest experience, and if it had been my first, I might feel differently about anal. But frankly, the uncomfortableness went away within a minute or so, and I thanked Sheri. She laughed and said she hadn't been expecting me to fuck Craig. I explained what I had thought, and she laughed again and patted my ass, which didn't hurt me at all.

I guess I'm remembering this so I can work with Sveta, make her comfortable with it. James will do what I say, but there's a limit to how slow you can be. So we'll have to give her ass a workout before, so she'll be ready for him. And I don't deny that it might be uncomfortable. Hell, I've had cocks in my ass that made me uncomfortable since then. But it's only a minor discomfort if you do it right. That, at least, is my opinion.

I never saw Javi again. Sheri probably did, but she didn't mention it. And I was perfectly happy to go back to getting fucked by Mike in the ass, although I kept looking. Eventually I found other guys, my own age and older, who were also interested in anal. And of course Mike's cock got much bigger, so now him fucking my ass is much tighter than Javi. But I love every minute of it.

I did see Craig again. I felt a little sorry for him, actually, because it seemed like his roommate was playing a joke on him. So I tried to apologize. He took it pretty well, actually; I think he knew I wasn't in on the joke. He said he really enjoyed having sex with me, but wasn't sure it would be a good idea to do it again. So my estimation of him simultaneously raised and lowered. He was more mature than I gave him credit for, but he didn't want to fuck me again. But I left it at that. Not every story can have a sexy ending.