Late Night Friends Ch. 01

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She begins training him for oral servitude.
1.5k words
4.44
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10

Part 1 of the 3 part series

Updated 10/17/2022
Created 11/13/2003
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bareman
bareman
38 Followers

We became close after my wife died suddenly. Although we were acquainted prior to that time, it was strictly casual, but during my time of loss, I really needed a sympathetic ear. As time went on, I cried on her shoulder more and more, and we began to know each other much more fully and intimately. After a period of several months, it was only natural that we took it to the next level.

Now I won't bullshit anyone by telling them what a gorgeous babe she is--as a matter of fact, she's a plus sized woman with an average looking face, but she has a great heart, an inner beauty that makes her a dear friend. She also has a very open mind with some deliciously perverted kinks to it. Just the kind of friend I needed then! My sex life with my wife had gone stagnant several years earlier, and my masturbatory fantasies had gotten raunchier and more vivid over time.

As time went on our late night talks began to get more suggestive and intimate. She would tell me about her lovers and their activities, and I told her many of my fantasies and desires in return. One night we were both exceptionally horny and her daughter was staying with a friend, so she invited me over. Ten minutes later I was knocking at her door and she answered wearing a lace teddy covered by a sheer peignoir. The initial awkwardness disappeared as our lips met and our tongues danced. We hastily explored one another's bodies with our hands, groping and feeling frantically before we even got the door closed.

Finally I kicked it shut and broke the embrace to begin undressing her. As I bared her breasts, I kissed her nipples and she threw her head back in pleasure, moaning how good it felt.

"I'm just getting started," I told her. "I want to lick you all over."

"Oh God yes," she moaned. "That's what I really need. Please lick my clit for me--I need to cum so bad!"

We moved to the couch and I began kissing my way down her body, moving deliberately slowly to heighten her arousal. I finally reached her crotch and kissed her pussy through the material of her teddy for a moment. I could smell her womanly scent and she was squirming and pushing her pussy harder into my mouth trying to spur me on to greater contact with her hard clit.

As I unsnapped the crotch of her lingerie, I at last saw her gash. Her lips were swollen with arousal and blossomed out beneath the sparse covering of pubic hair--an amazingly small bush on a plus-sized woman. Her vagina was tiny as well. I had seen bigger pussies on much smaller women, but I dove in and began licking her slit with gusto. By now she had hold of my head to guide it to the areas she wanted my tongue to contact and I enjoyed being "forced" to lick her most intimate places. It had been several months since I had been with a woman, so the flavor of pussy nectar was like water to a man lost in the desert.

She came quickly the first time, shuddering and shaking as her climax overtook her, arching up into my face and holding my head hard against her. "Oh God Tom! You have got a great tongue. I guess you weren't lying when you told me you love to eat pussy," she panted.

As I slid up her body, my cock was trying to burst out of my jeans and I rubbed my body against hers to stimulate myself. Janice reached for my zipper at the same time she reached around to fondle my ass. I lay back on the couch and raised my hips as she tugged my jeans down, exposing my six inch cock. She began to lick up and down the shaft while she fingered my balls. It had been a long time since I had gotten a blow job, and I lay back, reveling in the sensations her wet mouth was giving me.

Now I'm one of those guys who rarely gets off from a blow job, so she licked and sucked for about ten minutes and I still wasn't there, so Janice stood and shrugged out of her lingerie so she could straddle my manhood without interference. Putting her knees on either side of me, she grasped my cock and began rubbing the head at the entrance to her vagina, getting us both slicker for the initial penetration. Ever so slowly, she began to impale herself on my organ, her tiny pussy stretching to accommodate the head of my penis.

Her lips were slick with her dew and my pre-cum and she was so hot I thought I would get burns on my dick as she took me into her depths. Her labia had an almost rubbery feel from being stretched so tightly around me, and she took more and more of me into her on each stroke, until I was buried balls deep. I was almost delirious with pleasure as she stroked up and down my shaft, grinding her clit against my pubis every time she bottomed out.

I mauled her tits as she rode me, squeezing her nipples and moaning out her name. "Oh fuck Janice," I cried. "Your pussy's so hot! You're going to make me cum!" With those words I released my seed, coating her insides with my spunk, feeling like I might turn myself inside out I came so hard.

She stayed astride of me after my orgasm, slowly grinding her clit against my pubic bone as I caught my breath. After giving me a couple minutes to recover, she dismounted from my softening dick.

"Alright, that's enough time to get it together," she said. "Now it's time for you to get back to it."

I looked at her with a question in my eyes, not sure what she meant.

"Don't think you can come over here and fill my pussy with your hot cum and then just leave me with a wet sloppy pussy to deal with. Hell, it's already drooling out, now get your tongue down there before it makes a mess on my sofa," she commanded.

Suddenly something clicked in my head. I had told Janice about my fantasies of female domination and apparently she was taking it upon herself to help me live out a fantasy. "Yes Mistress," I said as I slid off the couch and to my knees between her spread thighs.

She was right, her pussy was already drooling, our combined juices starting to trickle down her gash to her puckered asshole, so that's where I started. As I applied my tongue, I was pleasantly surprised to find our combined flavor to be somewhat flavorful, slightly salty, but not distasteful. As I ran my tongue up her slit I encountered a thick white glob of my own cum as it oozed out of her cunt, so I scooped it up and quickly swallowed. I was really starting to get into this, diving into her opening to scoop out more of the remnants of our quick fuck.

"Yeah, you like that don't you?" asked Janice. "You might have some potential as a real pussy eater. Move up to my clit and lick there, too."

I was eager to do her bidding as I licked, sucked and nibbled her most intimate areas, careful not to let any cum get on her upholstery, enjoying being told what to do in such a forceful manner. Soon I was holding her labia open as I applied my mouth to her open vagina, sucking hard to get the last of my cum out of her depths. My cock was once again hard as a rock, responding to this erotic fantasy that until now had only played out in my head.

Janice was getting into the scene as well, grinding her pussy hard against my face, holding onto my hair to ensure contact where she wanted it most. She shuddered as I got her off again and again, coating my face with her juices. When at last she'd had enough, she commanded me to stand up.

"I want to see you jack off," she said. I hesitated a moment, embarrassed that she would ask me that. "It's not a request. Start beating your meat. I want to see you get yourself off."

I had never masturbated in front of anyone before and was bashful, but the authoritative tone of voice she used convinced me. I stood before her, stroking myself as she instructed, feeling very naked but very turned on. In a matter of minutes I was on the verge of cumming and Janice brought her face close to my penis. As I started to spurt, she put her mouth over the end of my cock and took all my semen into her sucking mouth. As soon as I finished, she grabbed my hair and pulled my mouth to hers, kissing me hard and forcing my own cum into my mouth.

"That will be all," she stated. "Go home now. I'll call you when I need your services again."

I dressed in silence and left, wondering what else she might have in store.

To be continued...

bareman
bareman
38 Followers
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AnonymousAnonymousalmost 6 years ago
I had similar encounter

I met a full-figured woman who said she was a pianist at a large church. I liked doing oral and she liked watching me. On two different occasions, I licked her to orgasm, masterbated, and had intercourse. It ended because I talked to her daughter about dating her, but cannot recall what I said. I was not sure it it was her trying to assert dominance or she was truly upset.

FailedscoutFailedscoutover 8 years ago
You Need Tag Lessons

Normally I pass over stories with tags like this. The tags are supposed to be used to tell a reader what types of sex or situations can be found in a story. Also they are a great tool for searching for stories with specific content.

Who would understand what the tag "Walked Bedroom" or "Couple Hours" mean anyway?

Who would search for "Friend Sandy"?

Su you went from 4 stars to two on each chapter.

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