Seducing Jennifer Pt. 09

Okay, dedicated readers. I hate to bitch but I've noticed that the vast majority of you are not voting. I know I don't vote as much as I should, but I feel like if I can't give someone a 5 or at least a 4, it's possibly better not to vote at all. If that's the case with the rest of you, I really wish you would at least give me a hint as to why you can't give me a 5. I welcome constructive criticism. And my ego welcomes massaging.

I held her in my arms all night, reveling in the feel of her small naked body molded against mine. We awoke several times to kiss and caress each other, but were too sleepy to do anything serious, even though my cock was soon hard and throbbing again and she was wet with desire.

When the first faint glow of dawn lit the room, we awoke looking into each other's eyes, foolish grins lighting our faces. "Morning, lover," she whispered. "A brand-new day, all for us. And today I'm no longer a frightened virgin. But I'd still like you to call me Anna."

I stroked her cheek with my hand. "I think you lost your virginity sometime last night."

"Not quite, but you were close to popping me," she giggled. "You showed remarkable restraint, Jack. Most guys would have rammed it all the way in and apologized later. If they apologized at all. And you didn't even come in my mouth when you had the chance. So you get A+ for self-control. You've come a long way since...well, you know." She grinned slyly. "You're almost ready to initiate a real virgin. But there are a few things we need to work on..."

"Like not getting caught jerking off into your panties," I said, my ears burning. She grasped my cock, which of course was rock-hard and ready for action.

"Not really, honey. Seeing that made me so hot I had to run back into the bathroom to get myself off. If I hadn't been playing Miss Innocent I would have jumped on you and sucked out every drop. And when I failed to lock the door, you should have come in after me, scolded me for being a prude, and carried me out to the bed to have your way with me. Girls who don't know need to be taught. Now, you've got me sopping wet again. So what are we going to do about it?"

I crushed her against me and kissed her hungrily, then rolled her onto her back and began a slow journey toward her pussy. Before I reached my goal she crossed her legs. "Lie on your back," she ordered. Apparently Little Virgin Annie had evaporated with the morning sun. She sat up, leaned down to take my cock in her mouth, and thrust her pussy into my face, her slim thighs over my shoulders. I nuzzled at her dripping snatch while she sucked my cock vigorously, tugging on my balls with one hand and teasing my asshole with the other. The distraction of eating her pussy was enough to delay my orgasm, and when I licked down her slit and plunged my tongue first into her hot snatch and then into her puckered asshole, she dropped my cock and ground herself against my face, her thighs quivering as she came all over my face. She rolled off me and switched ends again, cuddling against me as her ragged breathing slowed.

"Wow," she gasped. "I thought I was going to turn inside out. It would have been so hot if you had come in my mouth just before I went off...it's OK to do that now, you know. Since I'm an experienced woman, and I've learned to like it."

"I wasn't sure," I groaned.

"I'll tell you what," she said, raising up on one elbow. "If you think you can pull out in time, you can fuck my hot pussy. I'll leave it up to you. If you want to take the risk."

"Well," I considered, "I wish I could promise, but I was so close I'm afraid I wouldn't last long."

"Good answer, Jack," she said, stroking my cheek. "But maybe there's a way. Didn't you bring anything with you, just in case?"

"I do have a rubber in my wallet," I said, my excitement rising. "I'll get it." I jumped out of bed and dug my wallet out of my rumpled jeans, extracting the foil-wrapped package that had long ago made a circular imprint on the leather.

I crawled back into bed with her and fumbled with the foil packet, my hands trembling so much I could not tear it open. "Let me see that," Anna said, taking it out of my shaking hands. "Hmmmm...how long have you been carrying this around?"

"Uh, a couple of years? I figured, just in case..."

"Just in case you got lucky with my daughter," she teased.

"No! Well, kind of. I figured it was better to be ready just in case we got carried away, you know? But I didn't really plan to do anything to her until after we both turned 18 last month...."

"And I bet that circle on your wallet impressed the boys in the locker-room too, didn't it."

I blushed. "Maybe."

"Well, Jack, a little knowledge can be a dangerous thing. Look." She peeled open the foil packet and extracted the rubber, placed it on the tip of my prick, and began unrolling it down my shaft. Watching her do this was incredibly sexy, and my cock pulsed in her hands. "So when you push this into a tight pussy..." she tugged on my rubber-encased tool, "What happens?"

The rubber split and the head of my cock burst through. "Now that could be a disaster, couldn't it Sweetie?"

"Oh God," I groaned.

"You can't carry them around in your wallet for years, Jack. Or even for weeks. Even if you remember to use them at the critical moment, they're likely to break on you. And another thing: as big as your cock is, you need to get the magnum size. Even a fresh one can break if it's too tight and you get too rambunctious."

Oh God," I groaned again.

"And something else: One is not going to be enough for a man like you. So you need to have at least three handy if you're planning a full night of fun." She stripped the ragged remains of the rubber from my cock and tossed them onto the floor. "Oh, and one more thing: Nobody really likes to use these. There's nothing like a bare cock in a wet pussy. But luckily I do know something that's almost as good..."

My cock jumped in anticipation of her hot mouth engulfing my tool, but to my surprise she tugged at my shoulder and said, "Roll over."

I did as she said and she began rubbing my shoulders and back, then kneading my buttocks. "Just relax and trust me, Jacky. I know you'll like this." She bent over to tongue my quivering asshole, then slipped a finger into me, stretching my clenched hole. I tried to relax but her probing finger was making me very nervous. Soon she added more saliva and inserted another finger, stretching my hole uncomfortably. But in a way it felt good too. When she slowly withdrew her fingers I felt empty. I heard her pull open a drawer in the nightstand and in a moment she was back, kneeling between my spread thighs. "Unlike you, I thought to bring a few supplies," she said. A moment later a cold, viscous fluid spurted against my relaxed asshole and her fingers followed, lubricating me thoroughly. She withdrew her fingers way too soon, and as I started to protest I felt something else, smooth and cool, pressing against my back door.

"What are you doing?" I gasped into my pillow.

"This is a graduated butt-plug," she explained. I felt it slip into me past the first ridge, and it felt good, but I tried to squirm away when she kept pushing. "Just relax, Sweetie. You're doing fine. Only a little more to go...and in an hour or so you will be ready for something really exciting." More cold lubricant drenched my asshole, and I moaned as she steadily pushed the plug in past the second ridge. When it popped into place I was gasping and sweat was dampening my hairline. "Just relax, baby, only a tiny bit more..."

"Oh God," I moaned. "I can't take any more." She tickled my balls and kissed my neck.

"Sure you can," she whispered. "And guess what? As soon as you take it all, you get to do it to me."

I felt a thrill at that idea, and concentrated on thinking about how exciting it would be to do such a nasty thing to Anna's tight little ass. More cold lube slathered my asshole and the pressure began again. "Push back now, Jacky, like you're trying to poop it out. Don't worry, it won't come out." I did as she said, and a cramping pain tore through me as she shoved it all the way in.

"It hurts," I whimpered.

"Only for a minute, Sweetie. Now roll over and kiss me, and then it will be my turn."

Gingerly I rolled over onto my back, afraid that the foreign object would further penetrate my overstretched asshole, but it did not, and when she grasped my cock and started licking around the head I almost forgot about the rubber thing in my ass. "Mmmmm," she moaned. "You taste so sweet." She got back into the 69 position, poising her pussy over my face, and I dove in as she swallowed most of my cock, which was surprisingly not as hard as it normally would be. I slathered her pussy with the flat of my tongue before concentrating on her protruding clitty, and began probing her asshole with my finger as well, soon loosening her sphincter enough to insert two fingers. "If you keep doing that, I'm going to come, Jacky," she moaned around my cock. Oddly enough, I did not feel like I was close to coming myself. The rubber plug in my ass was no longer painful, but it was distracting.

She pulled her mouth off my prick with a wet pop. "It's up to you whether or not I get to come," she panted. "And to be fair I should tell you that I don't intend to let you come. So..." I attacked her clit with renewed vigor, reveling in the feel of her responsive body approaching orgasm. When fluid began leaking copiously from her snatch I knew she was almost there, and I withdrew my fingers and pulled my face out of her crotch.

"Nooooo!" she wailed, pounding the mattress with her fist. "You're so mean, Jacky!"

"I think you should wait," I said. "Unless you want to bring yourself off with your fingers while I watch."

"Oh, pooh. I think you know that wouldn't work at this point."

"Maybe not, but I'd enjoy watching you try anyway."

She rolled over, playfully slid a finger into her pussy, and held it up for me to lick. "That's what you're missing, you meanie." She retrieved another butt-plug from the nightstand and handed it to me along with a tube of KY jelly. I looked at the plug curiously. It looked kind of like a stack of three doughnuts of increasing diameter, and I understood why it had felt the way it did when she put the other one into me. "Maybe you should sit on the edge of the bed and hold me on your lap," she suggested. "It might make it easier for both of us."

It was an odd request but I went along with it, and was glad I did when I looked down at the plump globes of her snow-white ass so vulnerable in front of me. I massaged them with my hands, marveling at the softness of her skin and the tautness of the muscles beneath.

"I'm afraid I've been a very bad girl," she whimpered. "I prob'ly deserve a spanking."

I slapped one cheek lightly, hoping that was what she really wanted. Strange if it was. But kind of exciting all the same. "Really? What did you do this time?"

"I sucked a boy's cock," she whispered. "A really big cock. And he was someone else's boyfriend."

I slapped her again, a little harder. "Did you let him come in your mouth?"

"No! I mean, he did come in my mouth but I didn't want him to."

"You'll only make things worse for yourself if you lie," I told her sternly, slapping her reddening ass cheeks twice more.

She yelped. "I'm sorry! I mean I'm sorry I lied. I'm not sorry I let him come in my mouth. I wanted his come. And I swallowed it all."

"You're a very naughty girl," I said as I began spanking her in earnest. She kicked her feet and squirmed against me. "What else did you do? Did you let him fuck your pussy?"

"No! Not really...Ow!"

"How did you let him 'not really' fuck you?"

"I accidentally let him get just the head of his cock into me, and then I made him stop because it was too big and it hurt. Please don't spank me anymore!"

I continued to spank her lovely ass until it was glowing red and she was crying. I may have taken it a bit too far, but I found that I was enjoying it too much to stop. When I did make myself stop, I squeezed a dollop of cold KY onto each rosy cheek and massaged it in. "Now, you've been punished and you're forgiven. And here's a little surprise for you." I inserted the tip of the KY tube into her puckered starfish and squeezed, following it with a finger, and then the first knob of the rubber plug. She squirmed uncomfortably.

"Hold still or you'll get another spanking," I snapped. She stopped squirming and I added more lube and slid the plug in to the next notch. She moaned and I wiggled the plug around to loosen her up, then added more lube and pressed it home. She took it more easily than I had.

I helped her sit up and held her in my lap, my cock throbbing dully between us. She put her arms around my neck and I felt the tracks of tears on her cheeks. "Hold me, Jacky," she sniffled. "I need you to love me now. Even if I'm a naughty little white-trash slut."