Seducing Jennifer Pt. 11

Story Info
Jack takes Anna's anal virginity.
1.8k words
4.3
54.6k
18

Part 11 of the 30 part series

Updated 10/29/2022
Created 04/24/2014
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jacktar48
jacktar48
282 Followers

When I finally gathered the strength to crawl up on the bed, I took Anna into my arms and kissed her face all over, tender little pecks that ended with a full exploration of her mouth. I still had about as much strength as a newly-hatched chick. "So how did you like having your ass spanked and fucked, Jacky?" she said, gazing into my eyes.

"Not much," I admitted. My ass-cheeks still tingled and my asshole felt like someone had driven a truck up it. "I hope we don't have to do that again anytime soon."

She giggled and kissed my nose. "I promise I won't butt-fuck you again. At least not until you beg for it."

"That's not happening."

"You may be surprised...but the important thing is, you learned something, right?"

"I guess."

"Of course you did. You learned that you do not much like being on the receiving end. But as the good book says...'it is more blessed to give than to receive.' And you do want to give me some of what I gave you, don't you Sweetie?"

I nodded my head against the hollow of her neck, and licked at the sensitive line between her ear and throat. She moaned and squirmed. "I can't wait for that, Jacky. I'm a little scared, because I've never had anything that big in my ass, but I think you've learned enough to do it without hurting me. Too much. I know it's going to hurt. But I want to feel all of you inside me, and I want to feel your hot spunk shooting into me. No need to pull out this time, Jacky. Just hold me down and fuck me until you come."

My cock rose like an inflating tire. I was still weak and shaky, but I was ready to give it a try. She gently disengaged herself from my embrace when my hands wandered from her enchanting breasts toward her sopping pussy.

"I think we both need a little soak in the hot tub before we try that. And maybe a hot drink?" She rose from the bed and pulled me to my feet. My knees were still like rubber.

"Poor baby. Just remember this is what an inexperienced girl feels like after she gets fucked for the first time. Or even the second or third time. So don't expect her to hop up and start doing handsprings right after you've popped her cherry. Come on; I'll help you." She supported me as I shuffled toward the Jacuzzi. I was afraid to take long steps. It felt like my insides were about to fall out.

She helped me into the hot tub and I gratefully submerged up to my neck in the steaming water. I leaned back and let the bubbling jets massage away the soreness. She kissed my hair and turned away. "I'll be right back, Sweetie. You just relax and think about the nasty things you are about to do to me."

I watched her charming ass as she walked away, imagining bending her over and stuffing my cock into her tight little hole. And fucking that dusky channel until I busted a nut deep inside her. I was determined to make it last until she came at least twice. I closed my eyes and dreamed lurid visions of my heavily veined cock sliding in and out of her.

"Drink this, Jacky," she said softly. She had settled next to me in the tub and was holding out a large coffee cup. "Maybe it will wake you up." I took the cup and sipped. I didn't particularly like coffee, but this was different. It had a strong chocolaty flavor and was laced with whipped cream. And something else. A warm glow started in my stomach and spread outward to my fingers and toes. Good.

"Chocolate Irish coffee, Jacky. Drink it up now." I drained the cup, set it aside, and Anna climbed into my lap, straddling my hips. My hard cock was trapped between us, and she wiggled slightly, rubbing it against her flat stomach. I clasped her tight butt in my hands. If I lifted her just a few inches, my cock-head would line up perfectly with her pussy...

"No, Jacky! Sex in the hot-tub is really not such a good idea. And my pussy is still off-limits, unfortunately. So are you about ready to go back to bed?" I nodded eagerly and we climbed out of the tub, dried each other off, and walked to the bed with our arms around each other's waists. She stripped back the quilts and piled the pillows in the middle of the bed, then wrapped her arms around my neck and kissed me soundly. "Make me feel good, Jacky. I'm scared but I trust you. Just please don't hurt me. Show me how much you love me."

Apparently she was Little Virgin Annie once again. I pushed her back gently onto the bed and knelt between her thighs, parting them with my hands when she tried to cross her legs. I teased the lips of her slit with the tip of my tongue, tasting her excitement. Eating her pussy was becoming second nature, but I still loved every minute of it. I slid a finger in and out of her snatch as I sucked her clit, then began tickling her asshole as her breathing deepened. I timed it perfectly so that when she started coming I was ready to squeeze a big squirt of lube into her rectum. "Oh my God," she wailed as I followed the lube with two probing fingers. "It gets better every time you make me come. Fuck me now, before I lose my nerve. I want you so much, Jacky." She draped herself over the pile of pillows, her cute butt elevated for easy access. I got on my knees behind her and spread the cheeks of her ass with my hands. Her quivering pink starfish was at my mercy.

I pushed my rigid cock down and rubbed it along her dripping slit. It lodged against her hot opening and I couldn't resist letting just the head slide into her pussy. She squealed. "Not there, Jacky! Don't...I can't stop you, and I don't really even want to. But please don't. We shouldn't take the risk." Nevertheless I eased my cock into her steaming snatch up to the hilt and kept it there for long moments before regretfully withdrawing. I slipped one finger into her asshole and circled it around, stretching her while smearing a thick coat of KY onto my horny shaft with the other hand. Then came the moment of truth. I pushed the head of my cock against her clenched asshole and seized her lightly padded hipbones, pulling her back against me until the head popped into her. She sighed deeply and wiggled her pelvis. "Now go easy, Jacky. Fill me up, but do it slowly. Give me time to adjust to it."

I pressed onward and inward, savoring the heat and tightness of her anal passage millimeter by millimeter. I paused my invasion when she started to tremble uncontrollably. "It hurts, Jacky. Is it all the way in yet?"

I leaned over her back to squeeze her breasts. Her nipples were like hard little pebbles when I pinched them. Then I reached around her waist to rub her clit. And pressed onward. She was crying quietly into her fist when I reached the three-quarter mark, so I stopped again and started to withdraw.

"No, don't stop!" she wailed. "Give me a minute to get used to it! I want all of you in me! I want to feel your balls slapping against my pussy!"

I waited a few seconds, which seemed like forever, before I began fucking my cock into her ass with shallow strokes of no more than half an inch. I built up a slow but steady rhythm; back a quarter of an inch, in a half inch. Her breathing matched my gentle thrusts, a sharp gasp when I invaded new territory and a relieved exhalation when I pulled back. I felt no urge to come. I knew it would happen when the time was right. I concentrated on the wondrous sight of my thick brown rod stretching her tiny pink asshole, and at long last I was completely inside her, my coal-black pubic hair crushed against her tender white ass. After a few moments to let her relax, during which time I massaged her clit with two fingers, one on each side of it, I began to fuck her in earnest. She couldn't take more than about a three-inch stroke, and although I longed to pull out almost all the way and then slam into her, I restrained myself. My urge to come built slowly and surely, and when my balls drew up tight against the base of my cock I knew the moment was near.

"Stop now, Jacky!" she gasped. "I want to look into your eyes when you're filling me up with hot sperm!"

I held still while she slowly eased herself off my impaling rod. The sight of my throbbing meat-stick emerging from her greasy hole was captivating, although I felt a pang of guilt when I noticed the streaks of blood from her abused rectum. Then my cock was out of her altogether, her asshole gaping wide open. She rolled over onto her back and opened her arms to me. I knelt above her and she quickly guided my cock back into her dilated anal hole. "Now fuck me until we both come, lover. I want to feel you squirt inside me."

I began fucking her cautiously, but her hips rose and fell to meet my thrusts, and soon my balls were slapping rhythmically against her ass with every stroke. My urge to come had receded and I felt fully in control. I could feel the tension mounting in her taut little body, her copious pussy juices drenched my balls, and I knew her orgasm was not far off. At last she went over the edge and took me with her. She screamed when it hit her, then twined her fingers in my hair and looked into my glazed eyes when my first surge of come jetted into her. We writhed in each other's arms as we ground out our ecstasy together. Our waves of orgasm peaked, receded, and peaked again, the intensity decreasing until we were both exhausted, our hearts hammering against each other. I held her as she gasped for breath, my cock softening rapidly for once. Her asshole still gripped me like a velvet finger-trap, but soon enough my shriveled dick popped out of her, followed by a gush of spent come which stained the bed sheet pink.

jacktar48
jacktar48
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11 Comments
Rawmaster60Rawmaster60almost 10 years ago
To Anonymous

Friend the vagina and rectum are only a little distance apart. My love liked anal sex that way ass she got her clitoris massaged while the action was going on. More of an orgasm for her.

jacktar48jacktar48almost 10 years agoAuthor
Oh My, Anatomy Indeed

I'm tempted just to say "you'll understand when you're older," as I wonder if you are old enough to legally access this site. But I'll leave it at this: it is possible to engage in anal sex from a variety of approaches, both posterior and anterior. And I can prove it.

AnonymousAnonymousalmost 10 years ago
anatomy ?

Ok so it was going well until he started butt-fucking her from in front of her (with them facing each other). how does that work? in most humans the butt hole is in back...

jacktar48jacktar48almost 10 years agoAuthor
Thanks, OneEye

It's not what I expected when I started either. I'm not in charge anymore, just trying to keep up with the current.

The only destructive criticism has been from that one ignorant douchebag who is trolling the site and trying to discourage people. He accused me of padding the stat's so I suggested that he report me, and then I reported him. Haven't heard anything from the phony ass since, although I assume he's still voting '1' on everything I do. Maybe on everything anyone does, for all I know. No big deal. As long as people want to read my stuff, I'll keep posting it. I get free opinions, and the readers get to read a rough draft free of charge. Perfectly acceptable quid pro quo as far as I'm concerned. Surprising how difficult it is to get anyone I know to look at my stuff.

I can't say where the story is going, but I expect everyone will be together in the end. Somewhere, somehow. We'll all find out when it happens.

Thanks for your opinion. I'll keep it in mind.

OneIBlindOneIBlindalmost 10 years ago
Keep Going...

I think this has been one of the more engaging stories I've read in awhile. It's not what I expected when it started, but like all good stories; it's evolved quite nicely. My kids have a saying, "Hater's gonna hate!"

Don't sweat the naysayers who only want to pick apart your creation. I like the short story aspect. You cover a wide range of things in a chapter so there's no need to have multiple pages/chapters in one Part. I can't wait for Jack to practice all he's learned on Jennifer... with mom's watchful guidance of course!

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