tagAnalThe Descending of Jessica Ch. 04

The Descending of Jessica Ch. 04


You might want to read the chapters in order. Just sayin'.

Brent and I slept through the night. We had fucked ourselves to exhaustion and I had lost track of how many times he had made me cum. I had never slept in the same bed as a man, and after Brent and I shared my first fuck we fell asleep in our juices, my head resting on his shoulder. I was in love and the man I loved had satisfied sexually in ways I could never have imagined before. My sleep was filled with dreams of us together and whatever hormones gave one a sense of joy coursed through my veins.

Morning unfortunately came and with it, reality. I awoke with Brent spooning me and for a moment I felt as safe and secure in the arms of my beloved as an 18 year old girl could. Just a week before I had made a tragic mistake with another guy (see chapter 1) and then found the love of my life at the foster home we shared (chapter 2). Last night, I gave him my virginity in the most spectacular fashion, and found that he had a penchant for playing with and invading my ass. This morning I woke up in his arms and I felt nothing but love for Brent, well, love and his rock hard erection poking me in the ass. This would not do and I quickly slid away and sat up. Brent was still asleep, so at least this time his cock's attraction to my ass was innocent, unlike last night on the stairwell when he worked me into a frenzy and then stuffed his meat in my rectum uninvited.

I was reminded of the stairway moments later when I realized just how sore my ass was this morning. It literally ached, and I ran off to the bathroom hurriedly thinking I was about to have an accident, only to have one of the most painful bowel movements ever. Still, there was no blood so I figured I was okay. The soreness remained though, both in my ass and my pussy which had taken quite a pounding the night before. My pussy was different though, it was a good soreness, like one gets the day after a solid outing to the gym. Still, my lips burned ever so slightly raw and would feel tender all day. My pussy lips, not the ones on my face. Oddly enough my jaw was sore, probably from the several blow jobs I gave Brent's generous organ, and my stomach was queasy from skipping sustenance the night before, except for the hot protein Brent had fed me.

A hot shower revived me, but both my pussy and ass resented the scrubbing they got and protested by expressing themselves through burning irritation as the soap and scrubbie washed them clean. Truthfully I was still oozing so much sex juice from last nights romp that I would wear a panty liner all day. "Oh well," I thought, "I knew what I was getting myself into. No, wait a sec, no one ever tells you about that stuff, like don't try to wear a thong if your boyfriend took liberties with your asshole last night or it will irritate it as soon as you put it on." Panties were called for today. Nice, hip hugger panties. With little hearts.

My supervisor, Gail, had told me the day before I could work the concession stand by in shorts and a bikini top and that became my uniform of the day, every work day, for the rest of the summer. My make up regime in the morning could be limited to a touch of mascara, some blush, a dash of lipstick, and a liberal spraying of spf 45. I towel dried my hair, pulled in back into a damp pony tail, talcumed my girly parts, and I was good to go.

Brent was still asleep.

With an hour and a half until we had to be at work I debated letting him sleep, but I noticed my sheets had enough glistening dried sex juice stains on it that if someone came in with a black light they would have thought the Manson family had visited. They had to be washed, and Brent would have to get his ass out of bed so I could throw them in the laundry.

"Wake up sleepy head" I melodically whispered in his ear.

He continued to sleep, and the only reaction I got was a grunt.

"Wake up darling" I tried again.

More grunts, but this time he rolled over onto his back, the sheet barely covering him.

The sheet rose like a tent at his waist. Damn, he was still hard. I had heard of morning wood, but having never slept with a guy had no experience with it. I loved his cock and had experienced it in every orifice last night, but I had not seen it, or any other penis, in anything other than dim light. Curiosity got the better of me and I stopped trying to wake Brent, and just pulled the sheet down. His manhood sprung up, free from the confines of high count linens, and stood proudly aimed vaguely towards his stomach. The velvety head was a light plum color and roughly the size of maybe a small nectarine. The shaft was thick, I could not reach around it with one hand, and was covered with angry looking veins the length of its 7 to 8 inches. At the base, his golf ball sized testicles were close to his cock in a nice package. I wanted to suck him right there as I had done the night before, except I knew this would start another session and we would be late for work. Still, I wondered if we could get away with being late for a moment, then I decided to be a good girl friend and follow another course of action.

I reached for the nightstand where I had a bottle of lotion. I squirted a liberal amount in my hand then smeared it over both, rubbing my palms together to warm it some before I gently grabbed his cock and slowly stroked it up and down. A soft moan escaped from my sleeping man and I gently rubbed my hand up and down. When one hand tired after a minute or two I would switch to the other. After a couple of times with each, more lotion was required and his cock glistened in the light. When I added more lotion, I began using one hand to stroke the shaft, and the other to rub the head. He began bucking his hips slowly as I continued to massage his dick. For the last move I could think of I started one hand at the base and ran it all the way up his shaft then followed with the other the same way so I was constantly pulling in one lotion greased motion up his cock. My pussy became moist and I knew the liner would need to be replaced before we left for work. A drop of golden pre cum oozed out of the tiny hole and the top of his head, and readers of the previous chapters know what a sucker I am for body fluids. "Fuck the lipstick, I could replace that" I thought as I bent over and extended my tongue and licked the head clean of his precious cowpen's fluid.

"Ewww, bad idea" I thought as my mouth filled with the taste of hand lotion.

I sat up again and began jacking him off vigorously. Soon his eyes snapped open as he groaned and raised his hips off the bed. His cock swelled in my hand and hot cum erupted from its head and splashed down on his chest and rock hard abs. A second geyser shot straight up and splashed back down on my hand, while the next several just sort of came out of him maybe an inch before covering his swollen cock head and my hand with white pearly goodness. I again bent over and sucked the head clean of these more copious fluids and fortunately they tasted more like cum than lotion. After I sucked up all the sweet cream from the head of his dick, I sat up, scooped up a finger full of semen from a dollop that landed on his chest, licked it off my finger, and said "Good morning! Did you sleep well?"

"Uhhh, yeah" he mumbled, still in shock from waking up to the orgasm I had just caused.

"Good, get up, you need a shower and I don't want to be late for work."

"I'll just jump in the pool when I get there" he said.

Geez, guy's have it too easy sometimes.

I replaced the liner as it was already soaked with my gushy wetness. Brushed my teeth. Again. Fixed my lipstick, Again. Then once Brent was out of bed I pulled the sheets and comforter and threw them in the wash. I wasn't sure what setting to use for "remove cum, pussy juice, ass juice and saliva", you would think they would label machines better, but I figured since the linens were white, bleach, soap and hot water would do the trick.

Brent fixed breakfast and I was gleefully happy this morning. A new era began in my life and all was well. Then I took my birth control and noticed only one more yellow pill until the iron supplements. Damn. Aunt Flo was coming to visit the day after tomorrow. My biological clock, I just learned, had really bad timing.

In the extra time I had while Brent cooked, I loaded up my tablet with study materials for a matter I planned to research today. I could use the wifi at work as well, but some of the stuff might be blocked. After eating I brushed my teeth, again. When you live with a dentist you develop certain habits. "Hey! Maybe that is where my oral fixation of the last couple days came from!" I laughed inwardly to myself.

Breakfast was bacon, eggs, toasted bagels and juice, but I was still queasy from semen, and having ingested more just minutes earlier waved off the solids and had stuck to the juice.

We arrived at work just before nine and I almost had the door open to get out when Brent stopped me.

"Hey Jessie" he said.


"I love you. You are so special."

My heart fluttered.

"I love you too Brent."

"The thing is, if folks at the club find out about us" he began before I interrupted.

"I know. We can't act like we are boyfriend girlfriend, the scandal would ruin Allison." I smiled, before continuing, "But that doesn't mean we aren't. We'll just save it until we get home. Then rape each other. Deal?"

"Deal!" He smiled, "But its not just about sex. It just feels right to be near you and to have you as my partner. Does that make sense?

"More than I would have ever thought before yesterday Brent. I owe you for being brave enough to tell me how you felt. I'm glad you did, and as your reward for courage, you have me. Forever if you want." I replied, then got out of the car before he could say anything to ruin the moment. A tear of joy was welling up in my eye and the folks at the club didn't need to see me crying after the scandals of the last week.

Speaking of which, as a result of my infamous blow job video, young guys at the club started hanging around the concession stand, and once word got out that Brent was back, more and more girls began wearing their skimpiest swimwear and laying out by the pool. The first of these would begin arriving today, but more would come in the next few weeks as every guy thought he had a chance with the newest hot slut, and every girl wanted a chance with last year's stud. Life in suburbia continued onward.

But this morning I focused on my research and learned a few things. My next plan was accelerated by the pending arrival of my period. As much as I loved Brent, I didn't want him messing around down there during that time of the month. My periods weren't bad really, compared to some girls I knew, usually a couple Tylenol took care of the cramps and the bleeding was only bad for a couple of days. But during that time, I didn't want anyone down there. It was just too messy and private. So, I had to do a few things first. And the more I learned, the more it became necessary to skip lunch except for a protein shake in order to run a couple of errands.

I grabbed the keys from Brent and drove his car to one of the several adult stores that had sprung up in the area for a quick purchase that took longer and was more embarrassing that I had imagined, and I had imagined it would be pretty embarrassing, then by a drug store for a few more delicate items. I stopped by the house quickly and I was back at work in an hour, but was late to reopen the concession stand as I was in the restroom a few minutes longer than I had planned. No one noticed other than Brent, who came over to ask if every thing was alright.

"Of course, why wouldn't it be?" I asked, handing him his keys back.

"Just wondering, you took off. I had figured on having lunch with you." He said.

"I figured it would be best if we didn't hang out so much when we're here, ya know?"

"Jessie," he whispered, although no one was around the pool to hear him, "Just because they can't know about us, doesn't mean we have to act like we don't know each other."

"I guess you're right, I'm just paranoid I suppose." I replied.

"You sure you're okay? You seem to be in pain."

"I'm fine!" I said emphatically, "just a little sore is all."

He accepted this explanation without questioning why, as he thought he knew already. In fact I was in discomfort for a completely different reason, but he didn't need to know that yet. About 4 o'clock I took a couple of ibuprofen to help with the soreness I was feeling, and was happy to shut down the concession and leave work. I was feeling a bit better, if for no other reason than I could finally get home, and the ibuprofen was kicking in. Brent and I walked out together and as much as I wanted to hold his hand while we did, and I almost absent mindedly reached for his, we couldn't show our affections lest the world know.

Once at the car I signed and said "I'm glad that day's over."

Brent remained silent until we were out of the parking lot, then took my hand and asked "Honey, are you sure you're okay, I'm worried about you. You seemed like you were hurting all day, did I, I mean, did we tear something up?" His voice was almost tearful with concern.

I smiled and replied, "Yes, I'm fine, I just had to take care of a couple errands at lunch and it hasn't been really pleasant since then, I did some research online this morning about something I wanted to surprise you with tonight and it turned out to be less comfortable than I had hoped for, I'm fine, I'm not hurt in any way, I promise."

"Why would you hurt yourself to surprise me?" he exclaimed, and his tone ticked me off.

"I didn't hurt myself, its just not very comfortable to wear a silicon plug all afternoon to relax my ass so you could do me anally tonight." I replied.


"A silicon plastic butt plug. I bought a butt plug because its supposed to help me get ready so it doesn't hurt when you do me back there."

"Where did you learn that?"

"The internet" I smiled, then added, "I learned a few other things as well."

I played with my hair smiling at him as he drove. Finally he said "I don't want you to hurt yourself for me."

"For the last time, I haven't hurt myself, and its not for you, its for us. I've never been close to anyone like you, and I want you to be happy. I'm going to do all I can to make our relationship work, and if that means finding a way to give you what you want sexually, I'll do it. So hush. Besides, the plug kinda feels nice. It's the thong I had to wear to hold it in place that's chaffing me where someone shoved his cock up my butt last night that's irritating and I swear the second I get home I'm taking them off!"

We drove in silence until we were almost home, when Brent sheepishly asked "It feels good?"

"What does?" I answered.

"The plug."

"Yeah, its not bad, sort of sexy in a dirty, nasty taboo kind of way. You want to try it next?" I laughed.

"No, I'll take your word for it." he answered.

I asked him to get the bags from the back seat when we arrived as twisting around from the front or bending over from the outside of the car to get them seemed too challenging. We went inside and I went straight for my room with Brent on my heels. Once we got there I had some serious prep work to do.

"Brent honey, I love you but I need you to leave me alone for a while, I want you to make the bed, then go take a shower, I call for you when I'm ready, okay?" I smiled.

"Uh, sure hon, just one thing"

"What's that?" I asked.

By way of reply he put his arms around me and kissed me deeply, passionately, For a few minutes our lips entwined, but he didn't touch my breasts, or my butt. He treated me like a fragile doll that might break if handled too roughly. I hoped this would continue through the night.

I had read about anal sex online all morning and found a lot of advice on how to approach it from both reference sources as well as porn star interviews. From this information I had come up with my own plan, which was generally as follows: 1) avoid solid foods for 24 hours prior. Porn stars do this before doing anal scenes apparently. 2)wear a plug all afternoon so as to loosen up the muscles surrounding my asshole. 3) wash thoroughly. 4) use an enema from the drug store to clean out myself on the inside. Hold the liquid in my colon for as long as possible, then expel it. Flush without looking because it's kind of gross (this tip I picked up as I went through the steps.) 5) Use another enema just to make sure you got every thing out. 6) put lube all over the penis shaped silicon vibrator you got at the adult store with the butt plug and work it into your ass. Turn it on and keep working it deeper until you can take it all. This is pretty exciting and took most of the hour before I called for Brent. 7) wash thoroughly again. Scrub your butt really good even if it is still a little chaffed from last night. Tomorrow will probably be worse anyway. 8) use the little lube syringe I got from the adult store where I bought the butt plug and vibrator to fill my rectum with lube. 9) make sure Brent puts lots of lube on anything he plans to stick in my ass, including fingers. 10) have Brent wear a condom so I won't have to think about where his dick has been later if I feel like blowing him, and finally 11) get on all fours and back myself onto him so I can control the speed and depth at first. 12) after everything, wash the plug and the vibe and hide it where no one will ever find it.

I gave myself a liberal sprinkling of talcum and put on the emerald green garter and stockings, anything more would be wasted, then stretched out on the bed and called for Brent. I was nervous, but feeling very sexy and ready to try something nasty.

"You ready?" he asked meekly as he came in wearing a bathrobe. "I didn't bother dressing again."

"Smart move." I smiled. "Let's talk for a minute." I patted the bed beside me.

Once he was seated, and clearly very shaky, I continued. "Are you nervous?"

"Yeah, this has been a fantasy for so long, you don't know how much I love you for letting me try"

"That's we do for people we love" I interrupted. "And since yesterday I've been curious about it too. So lets try it, and if it works, great, if not, then we know it's not for us. Agreed?"

"Agreed" he replied.

"So there are few ground rules. If I say stop, you stop, right then, and pull out gently. Understand?"


"When the time comes, I want you to wear a condom" I pointed to a fresh pack of them on the nightstand. "That is so if it doesn't work out, thirty years from now when I have your dick in my mouth I won't suddenly think "ewwww this was in my ass once" Okay?"

"Okay." he smiled at my joke.

"This is lube." I said, handing him the tube. "Great gobs of it go on anything that is going inside my ass. Cock, fingers, anything. Understand? This is important."

"Lube, got it, wait, what about my tongue?" He grinned.

"Just make sure it's good and wet. Now, when the time comes, at first your are going to hold very still while I back myself onto you. I need to control the speed and depth at first. I could get hurt if I don't and I don't want that hospital trip explained to the Andersons. Okay?"

"Okay, but now you're worrying me." he said, concerned.

"Don't be worried, just be gentle. That's the key here I think. And I know you can be." I smiled lovingly. "Finally," I continued, "remember how you got me so hot on the stair way last night? I need you to do that again. I think what happened was you had my outer sphincter muscle relaxed and when you put it in I just felt a bit of pressure until you hit my inner sphincter. Its what caused me pain. Think you can get me that hot again big boy? I grinned.

"I can sure try" he smiled, before asking "wait, you have two sphincters?"

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