Aunt Annie's Anal Anticsbytjrabbit©
(youthful aunt introduces nephew to anal pleasures)
(nephew drops in for a pleasant chat with his favorite aunt and finds that she is wanting a deeper and more penetrating encounter)
My mom had two sisters, but it was my dad's only sister, Annie, who was far and away my favorite aunt. My dad was the oldest of seven siblings and Annie was the youngest. She was six years old when I was born. My parents named me Timothy Jack in honor of my two grandfathers; it was little Annie who dubbed me TJ; it stuck.
Growing up in the house with six older brothers it was destined that Annie would be a raging tomboy. When I was a youngster it was Annie who taught me to ride a bike, skate, fly a kite, and climb a tree, fish, whistle. and curse. As a teenager she took on the challenge of teaching me to drive. She always treated me more like a little brother than a nephew. Even as a young adult she never seemed to grow weary of having me hanging around. When I was going through puberty I had a tremendous crush on my young attractive aunt.
Annie had attended law school in New York and at the age of twenty-nine, after marriage to a college classmate, that had failed after three years, she returned home to join my dad and two other brothers in the family law practice. I was twenty-three and completing my first year of law school at the state university which was located a couple of hundred miles from my hometown.
When I visited Annie during my time home on breaks, I was pleased to learn that absence from each other had not dampened our close relationship. It was not unusual for me to drop by her townhouse uninvited and unannounced. She had not started dating again since her divorce, and although I went out occasionally, most of my time was devoted to my studies. When I visited, we would talk about the study and practice of law; we might have a couple of beers or a margarita;sometimes we would go out to eat or to a movie. We truly enjoyed each others company.
When I dropped by to see her late last Saturday evening, Annie came to the door wearing a long button-up shirt and a pair of panties. I figured the shirt must have belonged to her ex. I noticed that the top two buttons were unfastened and that she was not wearing a bra. I saw in an instant that she had been drinking much more than what would be normal for her. She wasn't exactly plastered, but she was well on her way.
She gave me a hug, a peck on the cheek and said, "Hey, come on in TJ, I was just having my own private party, enjoying a few margaritas, I just blended a fresh batch. You can party with me."
In an excited voice I said, "Sounds fantastic!"
After pouring the drinks she said, "Let's go into the den where we can get comfortable."
I said, "Comfortable is always good" and followed her through the house. We sat next to each other on a large fluffy sofa. Annie tucked her feet up under her butt and I stretched my legs out and rested my legs on the coffee table, taking care not to knock over the drinks.
With her speech just a bit slurred she said, "So, TJ fill me in on how things are going with you."
I said, "Just enjoying my time away from the books and classes."
She responded, "Yeah, I remember how hectic it was. There was a hell of a lot of pressure with the continuous reading, lectures, writing papers, and of course the exams. I thought the three years of law school would never end. I'm sure you feel the same way."
I said, "My first year seemed like forever, but, like you and dad, I do enjoy the study of law."
Our conversation shifted to family and friends. We told old stories about growing up and had a good laugh about some of the things we had done as children. She had to notice that my gaze would often be fixed on her bare breast peeking out from underneath her shirt instead of on her eyes. I was hoping she was not paying attention to the bulge that was growing inside my pants.
She stood up on slightly wobbly legs and said, "Let's have another round."
I said, "Yeah let's, but I'll fix them this time."
She said, "No, no, you stay right here, and relax, I'll get them."
I asked, "How many have you already had?"
She answered, "I think this is number four, but whose counting?'
"Not me!" I shouted after her.
When Annie returned with the drinks, I saw that the third button on her shirt had been unfastened and that her nipples were hard and erect. As she sat there next to me she would casually place her hand inside of her shirt and rub on a nipple for a few seconds. I kept thinking that the increasingly growing bulge in my pants had to be obvious to her.
I was taken by suprise when she asked, "TJ, are you getting any?"
I repeated her question back to her, "getting any?"
"Pussy, you know, pussy TJ?"
I felt a flash of heat rush into my face and knew I had to be blushing blood red. I responded, "Well, not in a while. Nope, hadn't had any pussy lately."
She asked, "But you do like pussy, right? You're not a virgin? You have had pussy before?"
My initial embarrassment when she had turned the conversation to sex was quickly diminishing. Considering the state of her undress and the explicit questions about sex, I knew this was leading somewhere, and I was very willing to follow wherever it was going.
I said, "Well, I can't say that I have a great deal of experience, but yeah I've had some pussy, and yeah I definetly like pussy. Fact is, I'm crazy about pussy"
She responded, "That's great TJ. I thought so. You didn't mind me asking did you?"
In an attempt at humor, I said, "No, not at all counselor. You can ask this witness anything. Just don't require me to take an oath on any answer I give." My attempt worked because she started laughing and spilt some of her drink down the open front of her shirt. She placed her hand inside her shirt and rubbed the liquid into her tits as if it were a lotion.
She said, "That was funny. I had forgotten about your sarcastic sense of humor. I like it TJ. Turns me on!"
Where I had been slowly sipping on my drink I found that I was now gulping. I went into the kitchen and fixed a third drink for myself and her fifth. I sure as hell wasn't counting.
When I returned and handed the drink to her, I took my place beside her on the sofa, intentionally moving closer this time.
She said, "I don't have to ask if you like tits TJ, since you haven't been able to take your eyes off of mine, and I can tell by the huge lump in your pants that they're doing something for you."
When I didn't respond she once again placed her hand inside of her shirt and massaged one of her hard nipples.
I agreed, "They are nice and you rubbing on them the way you are is playing a big part in causing my bulge to get bigger and harder."
She said, "Yeah, I know!"
She continued with her questios, "Let me ask you this TJ; are you anal?
I again answered her question with a question, "Am I anal?"
"Ass TJ," she said, as she reached down and gave herself a hard slap on the cheek of her ass. "Are you into ass?'
I said, "Yeah, I'm always checking out women's asses. Don't most guys do that? It's pretty standard stuff, isn't it?"
"That's not what I meant," she replied. Are you into putting your dick in a woman's ass? You know, ass fucking TJ?"
Before answering, I drained my third margarita and Annie, who had not touched the one I had brought her, slid it across the coffee table toward me.
"I said, "I've never given it any thought Annie, but I'm sure that I will think of it from now on when I'm checking out a nice firm ass."
She laughed and said, "After tonight, I bet you will!"
She said, "You know Larry and I had a lot of problems in our marriage but sex was not one of them. "My ex was a real ass man. We never once had sex that he did not finish by fucking me in my ass. That's where he wanted his dick to be when he would shoot his load."
She continued, "Don't get me wrong TJ, he loved pussy and he knew what to do to get me hot and ready. He was a great kisser! He would put his wet tongue into my ear and drive me up the fucking wall; suck and bite on my nipples; suck my clit and tongue my pussy. I would cum two or three times before he was ready to get into my ass. The best and hardest orgasm I could have is when he unloaded deep into my ass. I thought the top of my head was going to explode. My ass muscles would squeeze every drop of cum out of him. I loved it TJ; loved it."
She continued, "When he first asked me to lick and tongue his ass I told him that he was nuts. I told him he could smell, lick and tongue my ass all he wanted, but I was not going to do that to him. He was persittent and determined. he kept encouraging me and one night when I had had a few too many margaritas, just like I have tonight TJ, I said to myself, what the fuck, and told him to get on his hands and knees. I begin licking and tonguing his ass. The smell and taste and the pleasure he was experiencing was a huge turn on for me. I would jerk on his cock while eating his ass and when I felt him about to explode I would take his dick in my mouth and let him shoot his cum down my throat. It was great TJ. I would cum just having him shoot off in my mouth. Wasn't long before I became as much into his ass as he was into mine. I would strap on dildos and fuck his ass; use butt plugs, ass beads and vibrators on him. It was immense sexual pleasure for him and for me. He was a total jerk, but I really miss that part of our marriage TJ. My ass really misses it."
Annie slowly unfastened the final two buttons on her shirt and let it fall from her shoulders onto the sofa. She moved close to me and offered her breast for me to massage and suck. We kissed and she ran her tongue round and round in my mouth. I responded by sliding my tongue in and out of hers. Our tongues flicked together and she sucked and bit down on the tip of mine. She pulled my shirt up over my head and tossed it onto the floor and began kissing my nipples and belly, all the while rubbing on my throbbing hard cock. I rubbed my hand between her legs and felt the wetness from her soaked panties. I slipped a finger into her steaming hot pussy and massaged it. When I pulled my finger out it was dripping wet; she took my hand and sucked the creamy juices off of my finger.
She slipped her panties off and mounted my lap, facing me. She took her soaking wet panties and began rubbing them all over my face. She demanded, "Smell my pussy and my ass in my panties TJ. Suck the juices out of them."
She said, "Taste and smell are big part of sex you know?"
I moaned a "Yes I know" in response, as I sucked on her panties and breathed in the smell of her.
She rubbed her fingers through the crack of her ass and placed them under my nose, "Smell my ass TJ." She demanded. She stuck her fingers into my mouth and said, "Taste my ass TJ. Do you like that? Doesn't the smell and taste of my ass make your dick harder? You want to fuck me don't you TJ?
I groaned an "Oh my God, Yes! Let me fuck you now."
She gave me a soft gentle kiss and smiled. She said, "I think you just might prove to be a true master ass man TJ."
I reached behind her shoving a finger into her ass and said, "I think you could be right about that."
I placed my finger into her mouth and felt her begin to suck. She took my hand and placed it under her nose and took in a deep breath.
Breathing heavily she said, "You're making me want to get into your ass TJ."
Annie unfastened my belt; pulled my pants off and threw them across the room. She took a couple of pieces of ice from a glass put them into her mouth and then put her mouth around the head of my dick. The ice quickly deadened the nerve endings as Annie continued to suck and move up and down on the shaft of my cock.
She released her mouths grip on my dick, stood up and said, "Come give me a hand with something TJ."
I followed her into her bedroom. She flipped on the light and opened the doors to a walk in closet. She pulled a large box from the corner that had a shipping label on the side and was tightly sealed with heavy tape. Annie took a pair of scissors from a shelf and handed them to me, indicating that she wanted me to open the box. I lifted the box and placed it on Annie's king sized bed, cut through the tape and opened the lid. While I was working with the box she went to the bathroom and brought back a package of alcohol wipes. She returned to the closed and came back with a bed sheet which she spread out on the carpet.
She smiled at me and said, "Like a good lawyer a good lover is always prepared TJ. I'm a damn good lawyer, but you will find out that I'm a much better lover."
She moved the box on the floor, took a seat on the sheet and motioned for me to join her. She said, "Were going to need all the room on the bed in a few minutes."
The box was crammed full of new, unwrapped sex toys. She took the scissors from me and began to remove the toys from their packaging. She handed me the box of alcohol wipes and instructed me to sterilize each toy. As I wiped the toys I examined them one-by-one. There were an assortment of butt plugs, butt beads, wands, vibrating-thrusting rabbits, strap-on dildos, cock-rings, leather handcuffs and ankle bracelets, and an assortment of flavored lubricants.
Annie had a satisfied look on her face as she leaned over to kiss me and stroked my cock. She bent her head down, smelled and then licked on the head of my dick. She selected several toys, placed them on her bed, flicked off the lights, reached down, took my hand pulling me onto the bed and lay down beside me. We kissed passionately and gave each other tongue as I squeezed and rolled both of her nipples between my thumbs and forefingers. I moved down to lick and suck on her neck, then her nipples.
She moaned and said, "You want to eat my pussy TJ?"
Biting down hard on her nipple, I grunted, "Oh yes. I'm going to eat your pussy"
She pushed me onto my back and climbed on top of me placing her pussy above my face. I stuck my tongue into her pussy, moving it slowly in and out. She started pushing her pussy against my face trying to get as much of my tongue inside her as possible. She handed me a four inch long vibrator and told me to shove it up her ass. When I gave it a hard push she began to moan and to push against the vibrator. She was yelling, "harder TJ, pump it faster! Suck on my clit, suck harder TJ, harder, harder!"
I was sucking her clit and pumping the dildo into her ass trying to match her rhythm of pushing against my face and the vibrator. As she let out a deep groaning sound, I felt her body begin to shake violently; her legs were quivering and squeezing against the sides of my face.
She yelled out, "Oh shit I'm cuming hard TJ. Keep sucking me!"
When I felt her body begin to relax, I licked on her clit and gave it a final few gentle sucks and slid the vibrator from her ass. She collapsed onto the bed beside me. My face was flooded with her creamy pussy juices, they were running into my mouth, nostrils, ears, and streaming down my neck. She turned on her side, kissed me, and started licking and swallowing the creamy fluid from my face and neck.
She said, "Oh my God baby what an explosive orgasm! That was amazing, wonderful!"
She said, "Now it's my turn to do you big guy. "On your back again."
She picked up the leather handcuffs and placed them around my wrist, stretched my arms above my head and secured them to the headboard. The leg bracelets went around my ankles and she pushed my legs up toward my head and used a leather strap to tie the bracelets to the headboard. She shoved a pillow under my hips so that I was staring down at the head of my swollen-throbbing cock.
With my head elevated by two pillows and my ass sticking into the air I watched as Annie began licking on the shaft of my cock and sucking on its' head. I was moaning with pleasure as she shifted her attention to my balls, continuing her sucking action. She used her thumbs to spread open my ass and put her nose into my crack. She began sliding it in and out fucking my ass with her nose. She was licked my ass and shoved her tongue in and out. As she licked and tongued my ass my cock was getting even harder, if that was possible. The sensation she was giving me was mind blowing.
I watched as she wiggled into a strap on dildo and grabbed a small bottle of lubricant squirting a generous amount of the slick liquid into the crack of my ass.
She asked, "Never had a dick in your ass, right baby?"
I told her, "Definite4ly no, I'm sure I would remember something like that."
"No dildos or other anal toys," she asked.
"Nope none of those either," I responded.
She slapped the cheek of my ass and said, "I get to have the honor to be the one to fuck my nephews' virgin ass. How awesome is that?!"
I smiled at her and said, "You will be gentle with me Annie."
She giggled and said, "You don't want gentle honey, believe me you don't."
I said, "I'm in no position to argue the point counselor."
She responded, "Right, you're not are you."
She placed the head of the dildo into the opening of my ass and said, "A little pain at first baby and then nothing but pure pleasure."
She began to push the dildo into my ass; she was right abut the pain and I shouted, "Oh hell no, it's way too damn big."
She ignored me and continued to push the dildo into my ass. She said, "Take deep breaths baby, it's nearly there."
I did as I was told taking in deep breaths; suddenly the pain I had been experiencing was gone and all I felt was sensations of pleasure steaming through my entire body. With each in-and-out thrust the dildo was rubbing against a spot deep in my ass that made me yell out with pleasure.
I kept repeating, "Fuck me harder Annie. Fuck my ass deep baby."
She sensed when I was close to ejaculating and stopped the action. She would rub on my thighs and say, "Easy honey, take it slow and easy." Then she would start pumping the dildo into my ass while she furiously stroked the shaft of my cock.
After repeating the process of starting and stopping several times, she pulled the dildo from my ass. I yelled at her, "Hell no, I want to shoot off, let me shoot off."
She paid no attention to my pleading; picking up a strand of butt beads she began to feed them one-by-one into my ass. The beads were hitting the same spot as the dildo and I moaned with pleasure as each bead bumped over the hot spot.
I watched as she grabbed a rabbit vibrator and shoved it into her pussy. She took a firm grip on the shaft of my cock and began stroking as her mouth encircled its head. She used one hand on me and the other to push the thrusting vibrator into her pussy. Her sucking and stroking on my cock became more vigorous to match the pumping of the vibrator into her pussy.
I felt Annie's body begin to tremble and she yelled out, "Cum with me baby. Cum with me! Shoot your hot cum into my mouth."
She reached down and began to pull the beads slowly out of my ass and I felt something like an electrical shock wave move through my entire body causing me to shake violently. My dick began to jerk as I squirted her mouth full of hot cum. We were both moaning with the pleasure of our release as I watched her swallow the thick creamy liquid, licking my cock dry.
She unfastened the restraints on my wrist and ankles and left them dangling from the headboard. After we caught our breaths, I pulled Annie on top of me and we lay there in each others arms kissing tenderly. It was several minutes before a word was exchanged between us.
I broke the silence by asking, "Well Annie, am I now officially an ass man?"
She responded, "Not just yet TJ. Just one more activity and I will give you your ass man certification."
I knew that she wanted me to fuck her ass; to give her that massive explosive orgasm that she had described earlier in the evening.