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Cherry Picking

By Jon

(Older woman younger man, first time, oral, hetro, anal)

 

It had been a good workout. I was just finishing off with some bench presses before warming down. It was 3 o'clock on a warm Saturday afternoon and I had the place to myself, or so I thought.
As I got up from the bench I saw a woman watching me from the door. I recognised her as one of the aerobics instructors and, although I guessed she was in her late thirties, she had a body that any man would want to get to grips with let alone a horny 16 year-old like me.
"Er, hello" I stuttered.
"Hi, sorry to interrupt you but we are going to have to close early. Some workmen have ruptured the water main so we don't have any water."
"Oh that's ok I was just about finished anyway."
As I spoke I couldn't help looking her over. She was wearing a leotard that did nothing to hide her charms, in fact if anything the skimpy garment accentuated every curve and bulge. Her nipples looked as if they were trying to force their way through the material and the outline of her pussy lips was unmistakable.
At that age my cock needed virtually no encouragement to get hard so the sight of this sexy older woman displaying everything she had to me not only had the blood rushing to my manhood it almost had me cumming on the spot.
I looked back to her face and so that she was smiling and looking directly at my crotch.
I blushed furiously and turned around quickly. Thankfully the weights still need putting away so I used that as an excuse to keep my back to her as I said, "I guess I can't shower then, that will please the people on the bus."
"Oh don't worry about that, I can give you a ride home if you like, it's the least I can do seeing as we have inconvenienced you."
"Er, yeah that would be great. Thanks." My mind was in turmoil. I didn't want to appear rude by refusing her kind offer but at the same time I wasn't sure that I could keep my cock under control.
"Okay, I just have to go and check the rest of the building while you finish off in here."
With that she headed off in the direction of the changing rooms leaving me wishing that I could finish myself off. Instead, I put the weights away and tried to focus on other things.
By the time I got to the changing room to collect my gear I had just about got myself under control.
The woman was sitting on a bench waiting for me. She smiled and said, "we're the last two."
"Oh I'm sorry I didn't mean to hold you up."
"Don't worry I'm not in any hurry. In fact you could have a wash if you like."
Now I was confused, "I thought you said there wasn't any water?"
She stood up and walked towards me.
"I was thinking more of a tongue bath," she said as she grasped my re-swollen cock.
I tensed at her touch. For at least 2 years I had been dreaming and hoping for something like this to happen and now that it had I froze. My mind was screaming at me to respond to her but I couldn't move.
I expected her to get annoyed with me for being such a baby but her smile just got bigger.
"Oh wow, you're a virgin!"
It was a statement rather than a question and I knew there was no point in lying so I just nodded.
"It's ok baby, just relax and enjoy. By the time I have finished with you, you will know all you need to get the girls creaming their panties over you."
She took my hand and placed it on one of her tits. I gently rubbed and squeezed the firm flesh and was rewarded with a slight moan.
Once again I felt her hand on my cock and this tie I responded by pressing my hardness into her fist as she slowly wanked me through my shorts.
My other hand found her vacant tit and I started giving it the same treatment as the first.
"Have you ever seen a naked woman before?"
"Only in magazines."
She stepped away from me and pushed the straps of the leotard off her shoulders and then pulled her arms out so that the only things keeping the garment up were her tits.
"Well come here and find out what a real woman looks like, I think you'll like it a lot more than the magazines you wank off over.
With trembling hands I reached out and started to pull flimsy material down her body.
Her tits sprang free looking magnificent. Acting purely on instinct I dipped my head and took one of her plump brown nipples into my mouth. She gasped and held my head as if she were worried that I might stop. I flicked the bud experimentally with my tongue bringing another gasp. Her reaction gave me confidence and I started to nibble flick and suck for all I was worth. I found her other nipple with my fingers and began gently pinching and pulling it as she writhed and moaned.
All too soon she pushed my head away, "I see your not a complete novice." She breathed, "but there's more for you to see."
I smiled, secretly pleased with myself. In truth all I had managed before was a few clumsy gropes.
Once again I started to push the leotard down her body. When it reached her hips she pushed down on my shoulders forcing me first to crouch, then kneel in front of her. My face was now level with her pussy.
She gripped the front of the leotard and pulled it up so that her outer lips bulged as the gusset started to disappear into her moist slit. It was only now that I realised that she had shaved off all her pubic hair. With one hand pulling the material tight she used the other on the back of my head to push my face against her bald pussy.
The scent that filled my nose was almost overpowering. The other boys at school always said that pussy smelled like fish, but that was not how it smelled to me.
"Lick it" she demanded.
I hesitated, but only for a second. Then I stuck my tongue out and started to lap at her sex. I ran my hands up the back of her legs to her arse and started to kneed her firm buttocks as my tongue moved up and down her slit.
I carried on like this for a few minutes while she moaned and ground her cunt into my face, then reluctantly she pushed me away.
"Either you're experienced in everything but fucking or else you're a natural."
With that she pushed her leotard over her hips and arse and let it drop to the floor leaving her standing totally naked in front of me.

I wanted to bury my face once again, I wanted to taste and smell her again, but she had other ideas.
With a finger under my chin she encouraged me to stand again. Then she kissed me forcing her tongue into my inexperienced mouth tasting her own juice and apparently enjoying it very much.
She broke away and virtually ripped my tee shirt off me and she fastened her mouth to one of my nipples sucking and flicking it as I had done to her. The other nipple she pinched between her thumb and forefinger and pulled and tweaked it. It hurt but it also turned me on.
Then, still tweaking my nipple with one hand she moved her head down my body, her tongue snaking down me leaving a trail of saliva.
Then she crouched down, placed both hands on my hips and looked up into my face.
Her fingers found there way into the waistband of my shorts and I thought she was going to just pull them down, but instead she moved her hands round to the front and then pulled the waistband out.
She was still looking up at me so that I could see her lust filled eyes and the wet swollen head of my throbbing cock. Slowly she looked down until she too was looking at my cock. She dipped her head further and ran her tongue all over the head, licking the pre-cum off it. I thought I was going to explode, and, almost as if she sensed this she quickly pulled my shorts down sank her mouth all the way down my shaft and squeezed my balls at the same time. That was all it took for my prick to erupt sending spurt after spurt of my spunk down her throat. She sucked greedily enjoying it all. I was in heaven but at the same time I was disappointed. It seemed to me that I had just wasted the opportunity to fuck this woman and lose my cherry. It soon became apparent that she had other ideas.

"MMMMMMMmmmmmmmm. Just what I needed, nothing like young spunk."
With that she stood bringing my shorts back up with her. She slapped my ass and said, "come on lover boy get dressed your coming home with me."
She stepped backed into her leotard and pulled it up covering herself once again then she bent over and picked up my tee-shirt and threw it at me.
"Come on, I need your cock inside me, but not here."
In a daze I put my tee shirt on and followed her out to her car.

We pulled out of the car park and headed for her house. When she was in top gear she reached over and squeezed my cock. "Rub my pussy for me lover." Her voice was seductive and at the same time commanding, tentatively I reached over and started to stroke her cunt through the fabric. We were in town but she didn't seem to care if any one saw. I got more adventurous and moved the gusset to one side and worked a finger into her sopping pussy. My cock was as hard as it had ever been and I knew that I was definitely going to lose my cherry, but at that point I didn't know what this sexy woman had in store for me.
We pulled into her driveway. As soon as the hand break was on she leaned over and kissed me forcing her tongue into my mouth, while at the same time her hand found my dick and started to wank me off.
Once again I saw the chance getting my first fuck slip away as I was sure that she would make me cum again. But then she stopped and got out of the car.
I followed her to the front door, then on into her house. She moved through the house with confidence until we reached the front room. She pointed to a cabinet and asked me to pour her a drink, vodka, then she disappeared upstairs.
I poured her drink and then looked through her drink supply for something for myself. I wasn't sure what I liked so I tried a whiskey. It burned as it went down but it wasn't an unpleasant sensation. I set the drinks down on the coffee table and sat down. I could hear her moving around upstairs and wondered what she was up to.
My cock was so hard that I couldn't resist pulling my shorts down over my cock and stroke my hard-on. I almost lost myself in a wank fantasy when I heard her coming downstairs. Like a guilty schoolboy I quickly pulled my shorts back up. I was too late though; she knew what I had been doing. She grinned and said, "that's mine now, you don't need to touch it, I'll make sure that it gets enough attention."

My mouth must have been hanging open. She was wearing what I can only describe as a harness. Leather straps encircled her tits and fixed like a bra over her shoulders and around her back. Around her waist was a belt and attached to it another strap was buried in her ass crack and slit.
"You like?" Her grin had widened when she saw the look on my face.
I just nodded not trusting my mouth to make the right sounds.
"Come on lets give that cock some fresh air."
I stood up and slipped my shorts down. My hard, sticky cock caught on the waistband of my shorts and then sprang back against my belly making a slapping sound.
She giggled and reached down and did it again. I was blushing and feeling hurt as I thought she giggling at me. Seeing the expression on my face she became serious again.
"Sex is supposed to be fun as well you know, but as this is your first time I realise that this is very serious for you. Later you'll learn the importance of being able to make your lover laugh."
With that she kissed me hard forcing her tongue between my lips. After a moments hesitation I returned the gesture thrusting my tongue hungrily into her mouth.
Her hands, which had been resting on my hips, moved round to my arse. She started to squeeze and rub the cheeks while at the same time pulling me hard against her causing my hard cock to rub against the leather belts and her stomach. Then she used her hands too pull my cheeks apart and I flinched as I felt a finger tip softly rubbing my anus. She let out a throaty chuckle and said, "Just relax lover, we'll leave that area for today but you will soon be begging for attention there."
I wasn't sure what she meant but I had to admit that her finger felt good there.
My confidence was growing again now. I moved my hands to her shoulders and pushed her away slightly. She seemed a little surprised but didn't complain. I lowered my mouth to suck on one of her nipples again. She allowed me a few minutes to suckle before lifting my head.
"Time to put that big cock of yours to good use and get rid of your cherry."
Just hearing her say that seemed to make my prick grow even harder. I had always thought that it was actually quite small. I know now that she was being kind, her intention obviously too boost my confidence still further.
She unclipped the strap that was between her legs and let it drop to the floor. Then she lay down with her knees raised and legs wide apart. She reached down and pulled the outer cunt lips apart with her thumbs.
"Come on lover boy see how wet I am for you."
I was down on my knees between her legs in no time. I fumbled about a bit trying to get my cock inside her, before she intervened and took my cock in her hand. At first I thought she was having the same problem as me. Then I realised that she was rubbing my cock head up and down her pussy slit on purpose because she was moaning as she did so. Each time it passed her opening she allowed the head to penetrate just a little and, although it felt nice for me as well, I was impatient to bury my shaft in her moist twat. The next time she dipped it into her slick, moist hole I pressed forwards forcing my cock in further. She gasped and I thought I had hurt her so I stopped.
"Oh don't stop, fuck that beautiful cock up me."
I didn't need any further encouragement. I rammed my shaft into her until our pelvic bones met and my pubic hair was brushing against her bald mound. I rested there for a moment looking into her face. Her eyes were closed and her lips open in a silent O. Slowly I withdrew until just the head was inside her, paused briefly, then thrust in all the way again. Then instinct took over and I just pumped in and out like a piston in over drive.
I was going to cum. I could feel my ball bag tightening as my balls prepared once again to deliver their contents. My pace quickened as I worked my way to orgasm. I was almost there when she suddenly wrapped her legs around me and held me fully embedded inside her. I almost cried out in frustration but she was in control and there was nothing I could do about it.
Some how she managed to flip me over on to my back with her knees either side of me with my cock still all the way inside her. Then she grabbed my wrists and pinned them above my head. Her head was thrown back as she started to move her hips. Instead of moving up and down she gently rocked back and forth. Slowly her tempo increased, as did her moans until the rubbing together of our pubic mounds became quite painful. My gaze alternated between her swinging tits and the area where our bodies were joined.
I was no longer close to cumming but she obviously was. She was panting and gasping and moving like a woman possessed. Just as I thought she was going to pull my dick off the movement changed. She started to shudder and grind her pussy down.
I could feel her cunt muscles squeezing my cock as she came. She just stayed there like that for what seemed like ages, every time one of us moved even a little bit she shuddered violently again. Finally she just sort of collapsed to one side and I heard a sucking sound as my cock parted company with her soaking pussy.
"Oh baby that was wonderful." She must have seen the disappointment at not having cum inside her because she added. "Don't worry sugar, we're not finished yet."
Her hand snaked down to fondle my balls. I leaned over to suck her nipples thinking that I would be able to manoeuvre myself into a position that would allow me to once again get inside her.
"Oh no you don't, you've got another cherry to lose yet."
"What do you mean?"
"You have three cherries to loose." She said smiling. "The first you lost when you fucked my mouth and the second in my pussy."
I suppose I knew what she was talking about but for some reason I couldn't bring my self to acknowledge it.
"Lie down with your arms back behind your head. I'll be back in a moment."
I did as she said and she disappeared upstairs.
She came back a few minutes later carrying a tube of something.
Without hesitating she walked straight over to and knelt down astride my head giving me a wonderful view of the pussy I had just fucked.
"Like the view?"
All I could do was nod slightly.
"Aren't you glad I stopped you shooting your spunk up there now? It would be dripping all over your face by now." she laughed.
She leaned back and placed the tube in my hand.
"I want to feel your cock buried in my arsehole but first your going to have to grease it up a bit. And while your doing that I'll get you nice and wet."
She leaned forward so that she was on her hands and knees above me. Immediately she took me into her mouth and began sucking greedily.
At first I just lay there enjoying the sensation of her mouth on my cock. Then I unscrewed the top of the lube and squeezed some onto my hand. Moved back slightly so that I could get a good look at her arse. It was a glorious sight. Smooth firm buttocks enticing me. I pulled her cheeks apart and was rewarded with the sight of her tight puckered anus. I ran a lubricated finger down her crack and felt her gasp when it came into contact with her crinkled hole. I rubbed my finger around the hole teasing it and also making sure that plenty of lubrication was left there. Then I slowly started to push the finger into her arsehole. As I did so I felt her shudder and she pushed her cunt down on to my mouth denying me of my view but at the same time rewarding me with the taste and smell of a woman in heat.
I sucked and licked her pussy while working my finger into her anus. When it was in to the second knuckle I pulled it out about half way and then pushed it home again. I started a steady rhythm going, fucking her arse with my finger and licking and sucking her pussy and clit with my mouth.
Meanwhile she was sucking away on my cock but holding it tightly around the base to stop me cumming.
She paused briefly to say, "That's it baby, now get another one up there, your gonna have to stretch it a bit if I'm going to take this piece of meat up there."
I pushed her up a bit and groped around for the lube, then instead of squeezing it on to my hand I spread her cheeks again with the thumb and forefinger of one hand. I aimed the nozzle directly at her arsehole and forced out a glob of the gel directly on to her anus. The reaction was exactly what I had hoped for. She clenched her arse and squealed. The effect on my cock was truly amazing and if she hadn't still been gripping the base I think I would have cum there and then.
She lifted her head; "I'm going to get you back for that." She laughed.
I started to work the lube in to her arsehole and in no time I had two fingers buried in her.
As well is moving my fingers in and out I started turning them back and fourth stretching her tight ring still further.
After about five minutes she stopped sucking my cock and moved over so that she was still on her knees but no longer above me. Her head was on her arms, her knees wide apart and her arse high and inviting.
"Come on sugar, fuck my arse."
I was on my knees behind her in no time with my cock head pushing against her greased opening. I tried to push it in gently but soon realised that it was going to take more pressure for me to get inside her. I pushed harder and the head of my cock slowly forced its way passed her tight ring. The feeling was incredible. I continued to push and soon I was buried all the way up her arse.
I rested there until I got used to the tight heat that was enveloping my shaft.
She had one hand between her legs frantically frigging her clit. Looking back at me over her shoulder she gasped, "go on, fill my arse with your spunk."
With that I started pumping in and out of her, but I couldn't last long.
I exploded deep inside her spraying her bowels with my hot spunk. At the same time she convulsed. As she came her arsehole started to clench gripping me tightly milking me dry.
We both collapsed exhausted and just lay there for a while.
"There, all your cherries popped." She breathed.
"I still haven't come in your pussy." I reminded her.
"Come back tomorrow afternoon, and you can cum where ever you like. Right now I have to get cleaned up and you have to go before my husband gets home."
The thought that she was married hadn't occurred to me. In no time I was dressed and she was seeing me to the front door. She kissed me hard then pushed me out of the door saying, "I should be home from work about one o'clock, make sure your here."
The door closed before I had a chance to answer and I walked off in a daze.
It wasn't until I was about half way home that I realised that I didn't even know her name.


I welcome and comments and suggestions. If this story is well received I will write about my next meeting with her.

 

Jonnyrebel@lineone.net


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