Could Have Been Worse

Ah, but it also could have been better.

If you can't guess what I'm talking about, I'm talking about James and Sveta's first time with the anal lovin'.

I won't tell you exactly when this was, so there are fewer clues to James' identity. For all you know, it might have occurred yesterday, or last week. I likes me a mystery.

Okay, funning aside... I invited James and Sveta over, as I said, the day after his birthday, and the day after his birthday dawned, and over they came. I brought down some party refreshments (probably the mistake I made that day, but it was an honest mistake) and we stripped down and sat around and ate cupcakes and drank various non-alcoholic things. I've decided that I'm perfectly okay with giving them alcohol, actually; I drank when I was their age, and it's not like I'm softening them up or anything. But it didn't seem appropriate that day.

They told me about James' actual birthday. Sveta had hinted he had a surprise, but she wouldn't say what. She did, however, let him blow a load all over her back after they fucked and he pulled out, pulled off the condom, and exploded. I tsked and said they should be careful, because even something like that can lead to bad things, but my heart wasn't really in it. I guess they fucked twice and Sveta sucked him off once. He really had an eventful birthday.

Me, I think I might have been tempted to blueball him a little before the big day, but then, I'd let him bareback me and the size and strength of his orgasm would matter. Maybe it might have mattered anyway, because if he was hurting to cum, he would have been quicker in Sveta's ass. But anyway, he's hard to wear out; he can cum and cum and cum. Ah, youthful vitality. Even my Dad was known to go for fourths when he was a strapping young lad.

Anyway, James said Sveta had had enough of his cum on his birthday, but he wanted to ice my cake. He said it just like that, and I thought he was making a double entendre, but he took a cupcake and told Sveta and me to give it a good icing. We both laughed and I punched him playfully and then looked at Sveta questioningly, wondering if she wanted to get distracted from the main event. But she looked a little nervous, so I figured she was probably putting it off.

Well, James' cock tasted good with some of the icing on it, and when his balls drew up and he gasped, I stuck the cupcake over the head of his cock and let him cum into it. I miss playing with food; Mike and I used to do that a lot. Anyway, it wasn't really icing but a cream filling, but I ate it all up. I'll be honest; the taste of cum was pretty much drowned out by the taste of cupcake. If he'd cum more, and the cupcakes had been a little less sweet, it would probably have been different.

James basked in the afterglow and watched me lick icing and cum from my fingers while Sveta cleaned his cock off. Then he said, "Okay, so what's my surprise? I mean, I've already got the two of you fucking me, what else could a guy ask for?"

"Go ahead, blow his mind," I said to Sveta, and she grinned nervously and turned to James.

"James, I've really enjoyed being with you..." she started.

"You're breaking up with me?"

"No, no, it's not like that. I mean, I've enjoyed being physical with you, you know..."

"The sex? You enjoyed fucking me? Lexi won't tell your parents if you say that," he laughed. I'm not sure it was the right way to reassure her, but I wasn't going to butt in.

"Okay, smartass, I enjoy being fucked by you. I love you inside me. But there's something we've never done, and I wanted to give that to you too."

"Lexi said we had to use condoms..."

"No, I want you in my ass." James was surprised by this, I'm pleased to say. "I've been practicing with Lexi, and she and I think I'm ready for it, so today's the day you get to fuck my ass, James," she said. I think she was trying to sound dirty, but it just came out all cute. Maybe it was just the way I was hearing it.

"Are you sure..."

"Yes, I'm sure," she said firmly, which was, I thought, a good sign. She might have been being shy about it, but she wanted that cock in her butt, I'll give her that.

"Now you've got to be a lot slower with Sveta that you are with me, and use a condom and plenty of lube," I said, feeling it was the appropriate time.

"Really?" He couldn't believe it. "I mean... Sveta, you're so great. I want you to love this, the way Lexi loves it. I mean, I can wait, if it will make it easier." He was looking at me.

"Sometimes you've got to jump in the pool," I said sagely. I don't exactly know what I meant, but it seemed to work.

"Really, I've been practicing," said Sveta, also looking at me like she wanted me to reassure her. I wasn't going to because it was her decision.

"Okay baby," he said, and I realized that they didn't really use pet names around me. It sounded weird, like I was looking into their life from outside. It was pretty arousing in a voyeuristic kind of way.

"I'll give you space, but Sveta wants me here, and I want to be here, I won't lie," I said, backing up a little. "James, the condoms are next to the couch and the lube is with them."

He was thrilled, but he was still all business. I don't know what that says about him, frankly. I can be pretty businesslike sometimes, and maybe that's a sign of intimacy problems or something. In this case, I think business is the way to go if you're about to fuck someone in the ass their first time.

He rolled on a condom and lubed it up, and Sveta knelt on all fours and presented her rosebud to him. It looked really tight. I had a pang of doubt, but dismissed it. "Lube, lots of lube" I said, and James obeyed, dumping more lube than he should have started with on Sveta's rump. A lot of it dripped off, or went over her back. But the impulse was good, and I can always get more lube.

He seemed hesitant to touch her anus, so finally I came over and helped him start out. I held Sveta's hand with one hand, while with the other I helped James massage the lube around her asshole. "Now put a finger in," I said. "Slowly, slowly," as he started to press in and Sveta gave my hand a squeeze.

"Wow, you're so tight," he said to her. She grunted.

She was nervous, and it made her extra tight. He had to work to get one finger in, and once it was in she squirmed a little and grunted some more. I started to wonder if she really was ready, of if we should just have a fingering session now and maybe work up to anal, when she wasn't so hyped up. But still, I really wanted to see these kids fuck, with his cock sticking out of her butt. I really did. I'm a bad person.

"Okay, she can take another," I said, not totally believing it. But I figured she would tell us to stop if she really couldn't take it. She whimpered as he pressed another finger in. I drizzled a little lube over it.

Once he had two in, she was gasping, and her torso had sunk to the ground, leaving her ass heaving in the air. "Is she all right?" he asked.

"Fine," she gasped, and I didn't really believe her. "Just tight."

"I don't know if I can get my cock in her," he said worriedly.

"Let her get used to your fingers, then put another in," I said. Maybe I was being too eager.

"Another?" he said, like he didn't believe me.

"Another?" she gasped. I felt like maybe another was too much.

"It's the only way you'll be able to take him, sweetie," I said to her. "You were taking that dildo pretty well last time. Just loosen up a little. Don't be nervous. It'll feel great, just like when we practiced." It was a pep talk I didn't completely believe myself.

"Okay, if you think I can," James said. "I can feel her getting a little looser, I think. Should I try it?"

"Do it," she said, gritting her teeth. I think she just wanted it over with, at this point. I'm a bad person.

He stretched her anus wide with his third finger, couldn't get it all the way in, and she was panting and moaning. "I think I'm hurting her," he said.

"Sveta honey, should we stop?" I asked, feeling a little guilty, because she certainly sounded like she was in pain. No blood though, no cracks, no tears, nothing but maybe a bit too much stretching.

She didn't say anything for a minute, and I was about ready to tell James to pull his fingers out, when she finally said, slowly and softly, "No, I want James to fuck my ass, Lexi. I don't care if it hurts a little. My first time with James hurt a little too, and it got really wonderful."

"Well just try to relax, honey," I said to her, then to James, "Well, she says she wants to, but you'd better be slow as a snail when you penetrate her, or you'll lose her forever."

"I'll be slow, I'll be really slow," he said, like he was terrified. I helped him ease his fingers out of her, then poured some more lube into her slightly-gaped asshole. In truth, she was much wider than she had been during practice, and his cock wasn't three fingers wide. More than two, probably, but not three. Also, it wasn't knobby.

"Okay, get behind her and put the head of your cock on her asshole," I said. I even helped aim him. "Now push in. It'll be slow going at first, but once you're through the first part, she'll take you more easily." I hope, I added silently.

And then he was inside her ass. God, I could have cum right there if I hadn't been so preoccupied with making sure he wasn't hurting her. Her rosy pink pucker looked like it was shitting out his cock, rather than him pushing it in. Once the head was in her, the shaft slowly stretched her wider and wider. I wish I had pictures. Again I say, if you've never seen a tight young ass take a cock for the first time, get out there and see it. Sexy as Hell.

Sveta gasped at the penetration, but she didn't make as much noise, no moans of pain, and when I looked at her face, she wasn't as flushed. But then she gasped, "No, stop, I can't take any more right now." James stopped dead, and probably would have backed out completely if I hadn't restrained him.

"She's just getting used to you inside her," I said. "You've got to leave it there until she's ready for more."

Eventually she nodded, and James slowly, carefully, like he was afraid of splitting her, started pushing in again, little by little. She stopped him again when he was halfway in, and asked, in a slightly panicked voice, how much more there was. I told her she was doing great, and James said she felt great on his cock, and he hoped she was enjoying it too. I think that was probably wishful thinking.

Eventually, after more starting and stopping (a lot more toward the end; the last inch took forever, but I felt it was important for him to be completely balls deep in her so she could feel the most penetration she would ever feel from him) he was completely up her ass. I'll say this for James: he went slowly, carefully, was worried she was in pain, and basically was a very commendable first anal partner. I don't know if it was all that exciting for him, simply being in a tight ass without being able to enjoy it much, but he was thinking of her. He's had other tight asses (well, mine, and I don't know, maybe someone else he hasn't told me about) to play with; this was all about Sveta.

Then she said what I wasn't expecting, really, but was dreading nonetheless. "Oh, God, I think I'm going to be sick."

"James, pull out. Honey, try to hold on. I'll take you to the bathroom." Damn those cupcakes. I think if she'd been on an empty stomach, or at least not eaten a lot beforehand, it wouldn't have happened. James lurched back, which probably wasn't the best thing under the circumstances, but on the other hand I didn't want him to get shat on. I helped Sveta up and helped her upstairs to the bathroom, dreading that I wasn't going to make it and I'd have to clean the floors. Fortunately, my parents were both out of the house, so there was no explaining to do.

Once we got to the bathroom though, Sveta couldn't shit for a long time. It was like it had been packed into her by the cock. I didn't watch, understand, but I stood there with her, and she said that she felt like she had to take a shit but couldn't, and her insides were upset. Then finally it came, and I'll draw a curtain over that period.

It's not uncommon, is my understanding at any rate, to believe that you have to shit when you're getting fucked in the ass. But the cupcakes and excitement and nerves definitely upset her stomach, and definitely it was good that we stopped.

Once she came back downstairs, she started to cry as I was walking with her back to the basement. "I can't do it," she sobbed on my shoulder. "I thought I could..."

"Maybe not today, no," I said. "But he understands, hon. He doesn't want to make you miserable. And let's face it, no matter how long it lasted, you're no longer a virgin anywhere. Buck up, sister." I said this last with a grin, and she smiled a little through her tears.

"Will you help me practice some more?"

"I think what's important now is that you and James and I all practice together," I said. "You and I can only do so much. I mean, we could work for years and stretch your ass all out of shape, but you might still have problems taking a cock. I don't know why that is. But James is probably willing to try again some other day, and I'll be there."

"I wanted to like it," she said, tearing up again. "I wanted to be like you, just let him fuck my ass..."

"Sweetie, sweetie, I've got lots of experience," I said. "My first time wasn't like that." Not totally true; I mean, I didn't get sick, and I loved it from the first, but it wasn't like later times, I'll own. "I know you're disappointed, and I know maybe it wasn't great like you hoped, but he had his cock in your ass. He fucked your ass. Isn't that something?"

She smiled again. "Now before we go back to him, there'll be no more anal today, okay," I said kindly. "I think that's enough for today. But I also don't want you to think you have to finish him because you started him. And I don't want him to expect that I'll finish him. This is your special day, and I don't want to ruin that by finishing him if you don't want me to. He can finish himself if you can't."

"No, it's okay, you should finish him, it's his birthday and he hasn't gotten to fuck you," she said.

"Are you sure?"

"Positive," she smiled as she wiped her tears away. "But I think I'm done for the day. And I didn't even get to cum." She seemed more pissed than sad about that, which was a good sign.

"You come over tomorrow and I'll make you cum harder than James can," I grinned. Ah, propositioning teenagers. I'm a bad person. She grinned and nodded, and we were all smiles when we went back in to find James biting his nails with concern.

"Sveta's done," I said. "Not forever, but for today," I added, seeing his crestfallen face. "Don't worry. She wants to keep practicing with you." His face perked up at that. "And she says that since it's your birthday, or near enough, you need to finish up, and you might as well do it with me." His face definitely perked up at that, and his cock, which had been limp, perked up a bit too. He still had on the condom, which was, amusingly enough given the way the fuck ended, completely clean. Sveta must have washed herself out plenty beforehand.

I got on my hands and knees and reached back and slapped my ass. "Lube me up and go to it, cowboy," I said, and he was quick to obey. There's nothing like sex to take your mind off your worries. He used a little more lube than usual (well, a lot of times he doesn't even use lube at all with me) probably because he was still nervous, but the cock slipping into my rectum was still good as gold. I came as he penetrated me, just a little O, nothing fancy. I couldn't even keep it up because he didn't go fast enough (nervous again) and I didn't have a hand on my button.

I was tempted to tell him to go harder, but I didn't want to show Sveta up, so I made do with my fingers on my pussy and his pleasant, if soft, penetration in my asshole, and built up to another nice O before he gasped, gripped my hips, and came. I must admit, I can see why women might feel like they need to shit when they're being fucked in the ass; I had a momentary sensation of it myself. But that's part of what I enjoy about anal, I think.

The silly kid, he was still wearing the condom, so all his cum went into it rather than into my ass. But that's okay, because Sveta was in no position to lick the cum out of my ass, which I'd promised her. She watched from the sidelines, not entirely without arousal, but not interested in joining in.

After that, even though I'm sure James could have cum again and I certainly could have, they dressed and went home together, wrapped in each other. James was telling Sveta that he loved his gift and couldn't wait for more, and she was cooing that she wanted it again too. Ah, young lust, or love, or both. Me, I sat there and wished I had a cock on demand, because I could have used another romp, more vigorous this time. But it'll do. I got to see James in Sveta's ass the first time, and I'll undoubtedly get to see it again, and again until they work up to actually fucking. And I'll probably get other benefits too. God I wish I had another guy who could be with James and Sveta and I, so we could swap partners and do DP and things like that. Ah well.

So, to summarize, as I said, could have gone better, but it went okay. I don't think Sveta's as copacetic as she claims, but I think she will try again. And if nothing else, she really does enjoy anal play, with toys or enemas, and she may have a scat fetish. Who knows, maybe that's why she felt like shitting.