The Descending of Jessica Ch. 04

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Jessie92
Jessie92
499 Followers

"We all do. I know, I was surprised too." I deadpanned before breaking out in laughter.

"Is that all?" He asked.

"Yep, I think that about covers it."

"That's a lot of rules" He said, leaning down to kiss me as he dropped the bathrobe.

"Next time we'll use your ass and you can make the rules," I mumbled between kisses as he gently massaged my exposed breasts and softly pinched the nipples, eliciting my first moan of the evening. He kissed his way down my neck, softly pecking and slowly bringing my blood to a boil as he continued downward and visited my breasts and nipples with his lips and tongue as his hand wander down to my now moist pussy.

I reached out and took his swelling penis into my hand, feeling its heft as I began to slowly stroke it. I wished I could suck on it and tried to pull it close to me but Brent was unrelenting in his progress towards my waiting vulva. I opened my legs so his mouth could land on my clit and his cock was finally available for my attentions. He lifted his leg over me and we fell into a nice 69 arrangement. I couldn't take as much of him in this way, but I was able to engulf the head and an inch or so of shaft. He moaned his approval as my warm wet mouth began slurping on his now throbbing meat. His balls and ass loomed over me, and I reached around his toned thigh to cup his testicles in my hand, gently massaging them before I lazily dragged my fingertips up the crack of his ass. Again he groaned as he continued to rearrange the nerves in my clit with his tongue.

My pussy was now a frothy cavern of sex juice, and I was near climax when his fingers entered me, probing around inside my vagina, triggering and stimulating the nerves there. I moaned with his cock still in my mouth as he began to fuck my face with his cock and my cunt with his fingers. First there were two, then three inside me, I thought he might try four, but I began to cum first as his mouth sucked my clit and he lashed at it with his tongue. I bucked my hips against his face and relished the spark of ecstasy that coursed throughout me. Finally it felt just too good and it had to stop before I lost my mind. His cock had been buried in my throat for I don't know how many minutes as I writhed on the bed with his fingers fucking me, but I need to moan and groan and gasp for air so I placed my hands on his hips and with a bit of pressure signaled him to get off. His dick slid out of my mouth, dragging a slimy trail of saliva with it,and he rolled to on side as his fingers continued to explore my moist cavern. Damn I wanted his cock to replace those fingers and fill me up as he had the night before, but tonight I had promised myself I would give him something darker, nastier and dirtier that he desired. I rolled over to face his body and grabbed his wet, hard cock and stroked it, then got up on my knees beside him. He began to lift himself up and when he was briefly on all fours, I saw an opening and took my chance,.

With his hard dick still in my stroking grasp, I bent over and ran my tongue around his balls He froze in position and moaned softly. Then, with the tip of my wet, hot tongue I drew a line from his balls up the crack of his ass, lingering it at his tight anus and swirling it around as he had done for me last night. I knew the erotic sensation he was now feeling as he moaned his approval, having felt it myself. What was a new experience for me was the utter disgust I felt for doing such a nasty, revolting thing. It was repugnant that I would lick a man's shit hole and an abasement to myself to do so. Still, for Brent, I continued. I stabbed at his ass with the tip of my tongue but was unable to penetrate his dark shit pipe. I licked my way up the crack and asked "Do you like that baby?"

"Oh yes, yes... Yes!" He replied.

I went full in and stuck my whole face in his ass and sucked on his anus as hard as I could before again licking it like a kitten licks milk. The degradation I felt was gut wrenching, yet it turned me on fiercely. The revulsion I felt was at once emancipating me from my inhibitions and liberating me from the notion that sex could be taboo. My cunt dripped with fuck juice and my heart raced as the more disgusting I felt the hotter I became. I grabbed the lube and smeared some on his ass, then slowly slide a finger into his ass. It was incredibly tight, I don't' know how he had gotten two into mine the night before, and I fucked it in and out as the lube turned a light brown and the smell of his colon filled my nostrils. I nearly wretched, and this was enough for me. I pulled my finger out and wiped it on a towel I had thought to have ready tonight.

He asked me to continue, but I only said to him "No, it's your turn."

When my mother was arrested the last time, or at least the last time I knew as she lost custody of me afterward, it was for prostitution. Supposedly she had accepted $100 from an undercover cop to perform anal sex. Since then I associated anal sex with something prostitutes do for perverts. Now here I was, I had my first real boyfriend for less than a full day, and I was on all fours offering him my tight, pre lubed bunghole for his enjoyment, and had spent most of the day preparing for it. I loved Brent, and I loved that he loved my ass. I was happy to be degraded for him.

Brent began slowly, as before , kissing up and down my crack on each cheek. I laid my head on the pillow and reached back with both hands to spread my cheeks and give him access. He began to devour my rectum with zeal. Licking, sucking gently, and finally probing my dark hole with his tongue. All the prep work I had done was paying off as his tongue easily slid into me and he wiggled it, tickling my formerly tight asshole from the inside. I was moaning uncontrollably and craved his cock in me like never before after just a few minutes of his attentions.

"Brent, fuck me in the ass!" I demanded finally, anxious to see if I could accommodate his cock in my back door.

"Okay, let me get this condom on" he replied.

"Fuck the condom, lube it up and get it inside me now!" I implored.

"Uh, okay." was all he said.

I waited and felt the cool lube from his fingertips smeared on and in my asshole, then waited again as he smeared it on his cock. I heard him stroke himself a couple of times to make sure it was all covered, then heard the lid of the tube snap back. I lifted myself up, and leaned a bit forward.

"Put it right on my ass, now! Hurry!" I said.

He placed the head of his cock on my anus, and the tip of it went in just enough for me to feel a bit of pressure. Then I moved back onto it, slowly taking it in as it stretched my sphincter and disappeared within me. All the prep work had paid off. It wasn't without pain, I gasped several times as I took the length of his shaft in, but it was bearable. It certainly didn't feel good either, it was quite uncomfortable, but I could put up with it to make Brent happy. Once I felt his balls against my hot, wet cunt I knew he was buried within me. I rested for a moment, getting a feel for it all. I had never felt so degraded, disgusted or such loathing for myself, but I could put up with that for Brent too. My rectum and its surrounding muscles relaxed around his cock and I had never felt so full or hot either.

"Okay" I said "now fuck me. Gently."

He began sliding his huge cock in and out of me slowly, causing me to gasp in pain several times, but I wouldn't let him stop. After a few strokes the pain subsided and was replaced with a strange warmth that began to spread throughout me. I found that I could move my hips forward and back, and side to side, without hurting myself, and I began to fuck him too. We stayed very slow for several minutes, adding lube as it dried out by pouring it onto his shaft as he fucked my asshole. My anus began to burn despite the lube as he increased his tempo. Drops of his sweat landed on my back and he was suddenly pumping me very fast. He kept telling me how good it felt, and it wasn't feeling too bad now actually, I thought I could get used to it if need be, it was very sexy in its nastiness, but I wasn't ever going to cum from getting it back there. I reached between my legs without thinking and began to rub my dripping wet pussy as he pounded my ass. I was so turned on by it all that it took me only moments to feel that now familiar tingle inside as my orgasm began to build. He was screaming he was about to cum when I fell over the edge into sexual ecstasy. At the moment I came, my anus tightened causing me to scream in pain as it tried to close on the unrelenting hardness of his cock, and causing it to milk the seed from him as I felt him swell and contract as he pumped jet after jet of hot sperm deep into my colon. I was out of my mind with sex and was no longer in control of myself. I wanted more cock so badly right then as we collapsed onto the bed and my ass literally shit his cock out of me as I groaned in agony. Once he was out of me the pain was over almost instantly and rolled over and looked down to see his dick at half mast, a long string of cum hanging from its tip and its shaft covered in spent lube and my ass juices. I couldn't stop myself, I had to degrade myself more, it was like I was addicted to be used for disgusting things. I grabbed his dick and stuffed it in my mouth, swallowing the jism I milked from him as well as the nauseating slime that coated him.

Brent was at a loss for words and his innocent, sweet girlfriend became a total cock whore, but he counted his blessings I'm sure.

'My pussy ached for relief, but I wasn't going to get it from Brent's dick anytime soon as no matter how I sucked and licked it it remained soft. My heart rate began to slow and I began to come back to my senses. I stopped licking his shit juice covered cock and went to the restroom where I tried to throw up, but had nothing on my stomach. I used mouth wash and brushed but that just made the taste of my ass seem minty. I finally gave up, looked in the mirror and hated what I saw. My ass ached as if I had been stabbed. Cum leaked from me, as well as anything else that was in there. I was repugnant.

Brent came to the door and asked if I was all right, but I didn't answer. He opened the door to find me on the toilet crying and tried to hold me but I pushed him away. His words didn't comfort me. I sent him away telling him we would talk in the morning, and once my ass stopped leaking I showered and went to bed. I slept fitfully, unaware of whether I still had a boy friend or whether I even wanted one. I had put everything into his happiness, and lost myself to filthy degradation. I slept fitfully, my cunt still staved for attention, until I got the vibrator out, washed it thoroughly, and fucked myself to sleep with it, completing my humiliation. A well hung boyfriend down the hall I had to use a toy to get off.

The next day though, things got better. More on that later.

Jessie92
Jessie92
499 Followers
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6 Comments
AnonymousAnonymousalmost 10 years ago
Anal -- yuck!

Ugly.

Rawmaster50Rawmaster50over 10 years ago
Much better

5 stars again as you explore your story from an erotic and emotional side of the narrator. She keeps learning new things and how she can get carried away with the moment. Your lady is a well-developed character as is Brent. The feelings are true to life also. Please continue

AnonymousAnonymousover 10 years ago
Best so far

Jessie, this is without a doubt the best series I've read for a good while on Literotica, and this chapter is probably the best of the lot of them. It's not often the word gets used as a compliment, but this chapter was just so "real". Like others have mentioned, you perfectly describe the conflicting emotions of someone discovering their sexuality (let alone someone who has been exposed to similar "taboos" being carried out in a negative manner by the older generation!)

I truly look forward to Chapter Five. Keep up the fantastic work

Down Under Dude

AnonymousAnonymousover 10 years ago
Thank you for an amazing story.

To be honest, I can't stroke off to it; but I am thoroughly enjoying the story nonetheless. There is a refreshing honesty in it that is missing from so many stories. Thank you.

gemman1gemman1over 10 years ago
Very Good

Keep up the good work. Your ability to describe the conflicting emotions and they detail of the feelings is great work. You have a penchant for making the story line very good. I also agree that you should include at the other girls.

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