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Introduction:

I had been watching Jan since puberty.
A little back ground....... Jan and Steve were friends of my parents so I had known them since I was little. They had two kids that were around 8-10 years younger than me and I often baby sat for them. Jan was about 5'6" and I would guess around 140 to 150 pounds. She wasn't fat, in fact she was very small up top, with almost non existent breasts. But she had a wonderfully big round ass with thick thighs and calves. She had dark hair with gray streaks that hung around shoulder level. All in all, i guess she wasn't the most attractive woman in the world but she was decent and she did have that wonderful ass. I might never have really noticed her in that way if it weren't for circumstances.
As I said, I baby sat for them fairly often. When I was 15 or so, I got dropped off at their house. Jan was still getting cleaned up while she waited for Steve to get home. Her kids were asking her tons of questions in her bedroom and her door was open. I stood in the kitchen drinking juice and for some reason,15 year old curiosity I suppose, I slowly started inching to my right. As i did this, I was able to see more and more of Jan's room through the door. Inch by inch I crept, not really sure what I was doing. Suddenly, there was Jan, standing there in just her bra and panties, bent over the bottom drawer of her dresser. As I stood there, probably slack jawed, she stood up and turned around. I was pretty sure she saw me as I quickly began inching my way back to the left. I was sure I was going to be in big trouble, but nothing came of it (except me). Now that was just a glimpse, but it was more than enough to fuel my 15 year old fantasies. It was the beginning of several years of Amy and Dan (the kids) pounding on the bathroom door while I masturbated furiously to the thought of Jan walking in on me and offering to help. That particular night, I remember laying in Jan's bed after the kids were asleep and thinking about her in her big white panties and bra. I jerked off several times thinking about that fine big ass.
Maybe a year later I remember going to the beach with them. Everyone was there, my parents and my brother and sister and Jan and Steve and their kids. Over the years I became aware that Jan wasn't particularly modest. I think this was more because she was a mom with small tits and didn't think anyone cared than because she thought she was hot stuff. That day I became aware that her bikini top didn't really stick too close to her chest because she was basically flat chested. It kind of tended to just hang loosely from her shoulders. I still wonder how no one could have noticed as I stood around with the four adults talking to each other while I positioned myself for a side view of Jan's tiny chest. What an amazing surprise it was when I saw her humongous nipples. I'd had no idea they could get so big, atleast like the end of my middle finger and almost an inch long. I looked as often and for as long as I dared that day. When we got home of course, I went straight to my room and fantasized now about both her big ass, which had looked marvelous in her big bikini bottoms, and now her huge dark nipples. I imagined that she loved having them chewed and sucked on and came repeatedly to that image for quite a while.
Add to this the fact that Jan always wore cut off jeans in the summer that rode high on her thigh and little tops that showed off her pretty flat mid riff, and you've got the basics of a pretty good crush on my part. I would sit for hours and stare at her thick, muscular thighs all the way up to her crotch, alwyas hoping for a glimpse of her panties. The thought of Jan was the only saving grace when, at the age of 17, on Memorial Weekend, I found myself traveling with my parents to St. Ignace for a long weekend of camping with the Smiths (Jan and Steve). I was miserable; both my siblings had been clever enough to find friends to stay with over the weekend and apparently Jan's kids were staying with their grand parents. I was the only kid stupid enough to get roped into a weekend in the booringest place in the world with four old people. I had packed several books and was determined to spend most of my time in my tent reading. If you don't know, the water is too cold and the shore to rocky to swim or lay on the beach in St. Ignace. It seems like all there is to do is eat pasties and sit around. And that's exactly what happened a lot of the time.
When we got to the campsite, Jan and Steve had already set up their camper on one side of the fire pit. My parents proceeded to park their camper on the other side and I set up a small tent to the rear and between the two campers (I wasn't going to sleep with my parents). When I was finished, my parents were already sitting in chairs by the fire with the Smiths. I was pleased to note that Jan was wearing cutoff shorts and there was an open spot directly across the fire from her. Eagerly, I set up my own chair and settled in for some s'mores. For most of the night, I listened absently to the stories of Steve and my father as I shoved s'mores down my throat and tried desperately to see Jan's panties. Finally, when I could stand it no longer, I said goodnight and retired to my tent. I laid there for some time, dividing my attention between reading with my booklight, massaging my cock and listening to the sounds from the camp fire. I was terrified at that age that someone might suddenly walk in on me with my dick out and I would die of embarrassment. So I waited impatiently for everyone to go to bed so I could whack off. Finally, I heard the sounds of chairs folding and feet shuffling and I knew they were turning in. I shut my booklight off and squeezed my cock warmly as I waited for silence.
As I waited, squeezing my cock, I could hear quiet voices and a lot of creaking from the Smith's camper as they got themselves situated in their bed. My dick was rock hard as I thought of Jan's big smoot thighs. I tugged it lightly as I continued to listen. Eventually the voices subsided but a mild creaking continued. I wondered at this as I slowly pulled my cock out and began rubbing it with both hands. I realized from an occassional moan or grunt and the rythmic squeaking that they must be having sex! This sent my mind and cock reeling. I began to jerk myself off to the rythm of the creaking noise as I thought alternately of Steve and then myself pumping away at Jan's warm dark pussy. As their tempo increased, so did mine. I was soon pumping madly, passingly grateful that I wasn't on a bed since it would be squeaking like crazy. It wasn't long before I was coming all over myself. I shot so hard I got my cheek and forhead, which for me was a real shocker. I lay there in the aftermath, kind of winded, shocked and overwhelmed for some time. the creaking ended abruptly from their camper and I realized they were finished. I wasn't. I had to jerk off two more times before I was able to fall asleep.
When I woke up, it was daylight. I listened and heard no sounds. My watch said it was only 8:20. Slowly, I rose and exited my tent. I grabbed a coke from the cooler and sat down by the now cold campfire. My mom likes to walk in the morning so I figured she and Jan were probably in the middle of a multi-mile exploratory walk. Steve and my dad, I was sure were out driving around as they loved to do for some reason. Well, I was mostly right. Jan suddenly came out of her camper in a pair of sweat pants and a tee shirt. "Oh, you're finally up I see." Jan confirmed my earlier guess regarding the others, stating that she had not felt like walking. "They'll probably all be back around 9:00 or so. Why don't we go get cleaned up so we can all go to breakfast when they get back?" she asked me. I agreed that breakfast sounded good and went to gather my shower gear. As we walked down to the public restrooms, Jan made a lot of small talk. I was only able to mumble an occassional reply as I watched her ass cheeks bob up and down in those sweat pants, thinking of the night before.
When we got to the showers there was only one open. Now this is where things get a little strange. Jan said "Well, why don't we both go in and take turns. You can brush your teeth and do your toiletries while I shower and then I'll do mine. That way we can save some time?" I was a little shocked at the suggestion but it sort of made sense. These were those individual bathrooms with toilet, sink and changing area. While my dick was twitching at the idea, I was a little dismayed. I was sure that Jan was offering in a motherly way that indicated I was not really a grown up and therefore it was okay. Somewhat shamedly, I agreed. If nothing else, maybe I'd get a peek of something.
As we went in I was fantasizing uncontrollably about Jan in the shower, bent over with me pumping away. "So how do you want to do this?" she asked. I snapped out of my fantasy world, sure that she had read my mind. I realized that she meant the shower arrangement. I was sure I couldn't get naked in front of her... "Oh, you can go first while I shave." I mumbled, having a hard time looking at her. "How long have you been shaving?" Jan had a little bit of a grin when she asked me this. I told her I had been shaving for several years, neglecting to mention that it had been completely unnecessary for much of that time. She seemed impressed as she began taking her top off. My stomach tightened up as she turned her back to me. I saw her smooth back and light tan line from her bikini and I felt my dick hardening. She started removing her sweat pants and I thought I was in heaven. Just when I thought I was going to see something really good though, she told me I should turn around. Disappointed, I did just that. I went to the sink with my shaving kit and begain to lay it out. I looked at myself in the mirror and realized Jan's big bare ass was staring at me over my shoulder in the mirror, as she removed her sweat pants. It was amazing. I was staring raptly as she stood up and turned around. I felt like my lifes dreams were being realized as I finally got a good look at her bush. A huge triangle of thick black hair looked back at me from between her wide fleshy hips. Her stomach was smooth and tight and her dark purplish nipples were hard. She stood their naked and I realized she was staring at me in the mirror. I looked down immediately and mumbled how sorry I was. I realized then, to my horror that my cock was poking out of my pants and I was rubbing it up and down on the rim of the sink. I froze my hips and glanced up again to see her looking at me and sort of frowning, whether in deep thought or disapproval, I couldn't tell. Rather than say anything, she just went to the shower and pulled the curtain closed.
I stared at my pulsing cock and wanted to jerk off but knew I couldn't. Suddenly I realized that my turn was next. Quickly, I decided to get undressed and put a towel around my waist to avoid letting her see my shamefully excited cock. As I was fastening the towel around my guilty prick I heard her mutter an mild expletive. "Is everything ok?" I asked, sure that she was really pissed at me. "No, I forgot my soap and shampoo, do you think you could hand it to me?" she asked. It seemed her own voice was as shaky as mine and I wondered if she was crying because I saw her naked. I went to her and handed the shampoo through first. As our hands collided, I think we both kind of freaked because we dropped it. I felt so bad, I started to reach in for it and got a glimpse of her already bent over reaching for it. Again i saw her wonderful ass and was rewarded at my new angle with a shot of her heavy pussy lips surrounded by more of her thick curls. I immediately withdrew, not wanting another incident. My cock was raging as I stood there. Her soap was brand new and I asked her if she wanted me to open it. She said yes.
As I stood by the garbage unwrapping the soap my dick was dripping pre cum on my belly and my mind was running like crazy. I felt like I was on the verge of doing something illegal. I expected my mom, the principle and the police to all come busting in at any moment. I took the soap to the shower and handed it through. Nothing..... I chanced a peek inside and saw Jan leaning against the shower wall like she was being frisked. her back to me, the shower running over her head. This was the breaking point for me. I was sure I was going to juvey or jail or something. I stepped quietly into the shower and pressed the soap against her shoulder. "Do you want me to wash your back for you?" I asked. Jan's shoulders tensed and I knew I was in trouble. We stood like that for what seemed like forever but then she seemed to relax. In a low husky voice I hadn't heard before she sighed and said "That would be nice." I was definitely in Heaven now. I began to massage her back with the soap, working it into her shoulders. Jan would frequently make what sounded like a moan of dismay and I would feel my insides shrivel up. Then I would be rewarded with a sigh of contentment and my spirits would soar. Whatever misgivings she had must have subsided significantly as I worked my way down to the small of her back because the moans decreased and the sighs increased.
I got to her ass and dove in with gusto, kneading and rubbing. I kneeled down behind her with the ridiculous thought that atleast if things went no further, I would get one good look at her pussy from there. Luckily things did not end there. I massaged her ass and legs, rubbing her inner thighs but afraid to touch her swelling pussy. I could see the dark purple of her inner lips pushing out past her fleshy outer lips. Having never seen such a thing, I was simultaneously disgusted and more turned on than ever. I stood up and placed my hands back on her shoulders. I had left the soap on the floor and my towel had long since fallen off. I moved tremulously closer to her as I stared down at my cock bobbing closer and closer to her plump ass.
As my cock touched the top of her ass crack she kind of moaned again and I ran my hands down her sides from her arm pits to her hips. I began to run them up and down, each time a little further around the front of her body until finally my cock was pressed firmly between my belly and her back and I was running her large rubbery nipples between my fingers. I was throbbing, my cock almost hurt it was so hard. I briefly wondered if I shouldn't thank my prior nights masturbation for lasting this long. Jan sighed as I worked my hands down her abdomen to her thick black bush. It sounded like some last dam had broken inside of her. She turned slowly in my arms as I fingered her sticky cunt. While I had fantasized countless times about fucking Jan, I had never really thought about kissing her. That's exactly what happened though. I was briefly overwhelmed. There was a hunger and ferociousness in her that I had never experienced with the few girls my age I had been with. She practically drove me back against the wall as I groped frantically at the bottom of her ass. She drove her tongue into me and I thought I would suffocate. When she pulled back from me though, I found myself diving into her mouth in much the same way, suddenly thirsty for more. When Jan pulled back from me a second time, I looked at her face and saw a glazed, heavy lidded look in her eyes. She grabbed my hand and led me out of the shower to the bench in the changing room.
It was a little chilly and we both had goosebumps as she sat me down on the bench. I didn't know what she had planned but on impulse I pulled her to me. She straddled me with her big swollen pussy rubbing against my coller bone beneath my chin. I rubbed her ass hard as I dipped my tongue down to her cunt. At this angle I could barely reach the top of her clit as she ground wantonly against me. I savored the taste of her cunt, again shocked at how gross and how wonderfull it could be. Abruptly she stepped back from me and started saying something like "oh, god, oh, god" repeatedly as she turned around and bent over. "oh, my god, oh, oh" Slowly, she straddled my legs and reached down to grab my cock as she began to squat down. I stared in disbelief as she slowly rubbed the head of my cock on her thick moist pussy lips. Slowly, inch by inch she lowered herself on my prick as she repeated the mantra of "Oh, shit, Oh my god......" Today I translate this all to have meant "This is so wrong but I can't stop myself. Oh my god, I'm going to do this." My body was on fire and the chill was forgotten as I watched her ass cheeks spread apart with each inch it dropped. Suddenly revealing to me, her dark brown little asshole surrounded by little dark hairs. I couldn't believe it. I grabbed her hips and begain guiding her up and down my pole as I watched her little ass wink at me every time she dropped and turned her pelvis.
While I had always been fascinated by her big ass, I had never even contemplated her little asshole. I believe this may be the true beginning of my status as a self proclaimed ass man. With my left hand still on her hips, I placed my right hand on the small of her back with my thumb pointing down her crack. As she rode up and down, moaning quietly, I slid my thumb down until it covered her anus. Jan moaned a little louder and with that encouragement, I began to massage her puckered asshole. This must have been too much for both of us because Jan begain to spasm violently as I emptied myself deep into her cunt. It felt, of course like gallons, I had never had so many spasms during orgasm. We sat there for a minute breathing heavily until Jan kind of shook her head like she was waking up. "Oh, shit, we have to get around." She stood up and my thumb popped out of her ass. During the spasms it had worked its way in just a little past the thumbnail. I looked at my cock and thumb, probably thinking something like 'i'll never wash this cock or thumb again.'
Jan kind of half smiled at me and gently suggested that I get moving. Dumbly, I did as she asked. When I looked at my watch it was 9:05. I rinsed off quickly, skipped the shave and put my tootbrush in my mouth as we left. Jan stepped out first to see if anyone was around. When she gave the all clear sign, I joined her and we headed up the hill to the campsite. Talk about a close call. At the top of the hill I could see my dad coming down. They had all just gotten back and were ready for breakfast. Jan laughed and said it was my fault for getting up late. I just stared at the ground. I was sure my dad knew what had happened and I couldn't look him in the eye. When we got back to the campsite, Jan talked like nothing had happened and no one seemed to suspect anything. I think my quiet surliness was taken to be normal for a 17 year old camping with his parents. We went to breakfast and spent much of that Saturday doing nothing. I spent a lot of time trying to read, but all I could think about was Jan's amazing pussy and that tiny brown asshole winking at me. I tried several times to make eye contact with her, looking for some indication that she felt the same way but she was completely closed off to me. While she wasn't mean or anything, she seemed completely indifferent. After an interminably long day, I went to bed feeling despondent. This didn't stop me from jerking off several times thinking about what I would do to her if I ever got the chance.
The next morning I was awake as soon as I heard voices. It was around 7 am. I could hear my dad and Steve talking about heading up to Tequamenon Falls and my mom was saying something about walking five miles atleast because she wanted to be ready to walk across the bridge tomorrow. I was straining my ears as I listened to Jan reply that she would like to spend some time cleaning around the campsite. My cock was hard as I lay quietly waiting. After yesterdays silence, I was sure I was never going to have another chance with Jan. Part of me clung to the hope though and I shook my dick lightly thinking of what might happen. As soon as I heard my dad drive off with Steve, I poked my head out of my tent. My mom asked me if I wanted to walk and I said "no thanks." She shrugged and walked off, leaving Jan and I staring at each other. She was wearing a big bathrobe with a towel around her head, obviously she had already showered. I approached her anyway with hope in my eyes. She smiled and shook her head. "Why don't you run down and get cleaned up and when you get back we can talk?" I'm sure I sagged visibly and she said "Oh, don't look so down, it's not as bad as all that." Well maybe not for her but I was despondent. Obediently, I went to the shower and got cleaned up. I couldn't even enjoy myself as I masturbated. When I got back Jan was no where to be seen. She must have heard me shuffling around because she called from her camper for me to come on in.
Inside Jan was cleaning the kitchenette and coffee was brewing. "Have a seat" she told me. Without looking at me she began. "What happened yesterday was inappropriate......." I hung my head. "I've love Steve and we've been friends with your parents for years. I don't want to jeapardize that." I was hurt but I understood somewhat, Just yesterday I was sure everyone would hate me if they found out. I kind of zoned out as she continued her lecture. I nodded dumbly as I thought about all the wonderful things I wasn't going to get to do to her body. "...and that's why we have to be more careful if we are going to do this. You can't be looking at me like you were, and we can't do anything to give this away. Do you understand?" It took me a minute for this to sink in. This wasn't what I expected at all. I nodded eagerly and said yes. I figured as long as I understood what was going on, I could handle it. She smiled with relief, apparently she had been pretty concerned by my own expressions while she was talking. She grabbed my hand and led me to the bed at the back of the camper. "everyone should be gone for atleast an hour and a half." I felt like I had won the lottery.
Slowly I removed Jan's robe and drank in the sight of her body. She practically glowed as I told her how often I had thought of her over the years. She told me that no one had looked at her the way I did for a long time. Feeling pressed for time we lay down and I quickly had my cock inside of her, pumping away. I told her how I had listened to her and Steve the other night and how excited I had been. She responded by wrapping her legs tighter around my waist and telling me that Steve didn't feel as good as I did. like a good boy, I picked up the pace with those encouraging words. Only moments later I came inside of her and we lay there not moving. I sucked gently on her collar bone and neck and she rubbed my back and ass a little. She started to say something and then stopped. Then she started again and I looked at her. Her voice was timid and her eyes looked a little scared. "Yesterday, when we were in the shower, you had your hand on my back......" I somehow understood that she was leading up to my thumb in her ass and I Interrupted her. I told her I was sorry but I couldn't help myself because it had looked so amazing. I was afraid she'd get mad, but I told her how I had thought of her little asshole all day and how I had even sniffed my thumb and tasted it, imagining i could smell and taste her. She was smiling dreamily as I finished my admission. "I liked it too," she began "more than I ever imagined. No one has ever touched me there but it made my whole body tingle when you did."
I was electrified. I asked Jan if she wanted to role over for a massage. Eagerly, she did. I admired her big white ass, outlined by a slight tan line. She spread her legs so I could kneel between them. I stared raptly at her puffed up pussy. I could see my come gathering thickly around her hairy opening. I didn't even bother with her back as I immediately started rubbing her big warm ass cheeks. She groaned with pleasure as I began moving her ass cheeks in opposing circles that rubbed them together and then spread them wide for a quick peek at her little brown asshole. She appeared to be flushed from her crotch all the way back around her ass. everything was a ruddy purplish brown and she was gyrating her hips slowly as I massaged her ass. I moved my hands down to the bottom of her ass, nearer her rectum and pointed both my thumbs down so they pressed againste her thick pussy lips. She really seemed to like this as I rubbed her pussy lips back and forth along with her ass cheeks. I was practically in a trance as my hands moved along her ass cheeks closer and closer to her puckered, hairy sphincter. I was leaning pretty close with my cock raging when I drooled right in the crack of her ass. She let out a low moan and I knew I was on to something. Quickly I dripped a little more saliva on her ass and changed my hands. I cupped her pussy with my left hand, leaving the thumb on her clit, slowly rubbing her. I placed my other hand on her back with my thumb over her asshole and began rubbing. Almost immediately her ass began to shake with orgasm. She sighed with delight and her ass kind of opened up to me just as it must have the day before. My thumb suddenly slipped inside of her a little and I held it there.
We held that position for a minute and I leaned down to kiss her ass cheeks. Jan liked that and I did it for a minute then I drooled a little on her as again and let it run down to my thumb and her ass. with my other hand I gently scraped some of the come and pussy juice that was accumulating just inside her outer lips. I added this also to the mix that was allowing my thumb to now slide in just past the knuckle. I told Jan what an amazing ass she had and she responded to this by relaxing her sphincter again and letting my whole thumb in. I just stared at it, my thumb completely engulfed by this amazing ass. My left hand wandered back down to her cunt and I inserted my other thumb. This seemed to get her revved up again because she started humping her hips again. Slowly we got into an in and out rythm that she really seemed to like. As one thumb slid out of one hole the other would be sliding into the other. It was incredible. I was so turned on, my cock was standing at full attention again as we did this. "Jan, do you think I could..." I didn't quite know how to ask, but I didn't have to. "YES" she replied. "I want you to, right now. Slowly I removed both thumbs. The hand on her pussy, I saw was immediately replaced by her own. She quickly slid two fingers inside of her cunt and buried her face in a pillow. I spit on my cock and rubbed it in with a surprising amount of pre cum. I placed my cock against her asshole and pushed slowly. It slid in easier than I thought. Man her ass was hot. I hadn't felt this much heat in her pussy and it was awesome. I pumped slowly in and out of her ass and occasionally I felt her fingers tickle my balls. I was afraid of hurting her but I didn't need to be. before too long Jan was thrusting her ass hard against my cock and we were fucking at a furious pace. I loved the feel of her hard ass cheeks pressing against my abdomen. I knew I never wanted it to end but there wasn't much I could do to stop it. Jan seemed to cum repeatedly and finally shot my load into her ass. I missed her already as I pulled my glistening cock out of her. I watched her asshole slowly close and felt my cock twitching again already. We lay there for a while and I rubbed her ass and her bellly and sucked on her big nipples a little while we talked quietly about how it had felt. It was difficult at first as neither of us was real comfortable talking about ass, didk and pussy, but it got easier as we talked.
We did manage to get together briefly the next day before the weekend was over. Since then, we get together every chance we can. The Smiths moved out of town so it never happens as often as I like but around holidays and once or twice a summer I make sure I can got camping with my parents. We continue to become more comfortable with each other and have tried a lot of things. I love having her suck my cock and eating her pussy and every position we can come up with is good. But the best thing is still always her ass. I can lick her little asshole for hours and being inside of her is still the hottest experience I've ever had. Jan is 55 now and I'm 33 and it just seems to get better and better. As a bonafied assman I'm constantly on the look out for a sweet new ass but I've never found one as great as Jan's, my first.
71 comments

anonymous readerReport

2013-09-24 20:43:26
I could last for hours fucking pussy, but as soon as I stuck my finger in her ass, that was the end of the line, I'd unload every time. If I was banging her butt, I couldn't last long, about a half hour the most.

HRW

anonymous readerReport

2013-06-01 22:29:19
Well obviously with a towel wrapped around the guys cock it was pressed up against his stomach............hence pre cum on the belly.
Great story btw.

anonymous readerReport

2012-09-04 20:02:12
how can your dick drip pre-cum on your belly whiles you're standing

anonymous readerReport

2011-05-15 15:23:21
amy and dan? the 39 clues refernece?

Anonymous readerReport

2010-06-15 05:16:00
Bro that was great i jerk off like 4 times on this stories

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