Top 20 #02 Ann

Ann and I met on a blind date after emailing each other on a mainstream dating site. Her proflle seemed to be a good fit for the kind of woman that I am attracted to. Her face-shot picture looked a little fuzzy because it was cropped from a larger photo but showed a very attractive, pretty woman. My profile included the information that I'm attracted to women who wear high heels and short, sexy dresses and skirts.

We set up a casual date for after work and she was much prettier than her photo, a petite knockout, long, jet black hair, huge, doll-shaped, blue eyes on her extremely pretty face, a super fit body dressed sharply in an above-the knee-black skirt, stockings, black pumps and a matching black jacket that covered a tight, rusched silver top that accented and displayed the outlines of her c-cup tits.

We met in an upscale restaurant, at the bar and had a nice date and i was definitely attracted to her, but there was a problem, her advertised age was 5 or 6 years under her actual age. She explained that she looked and acted younger than her real age and that she wasn't attracted to guys her age or older. I really couldn't blame her, since she looked about 30 rather than her actual age of 40 and was as fit as any personal trainer I've ever seen. But I also didn't think dating someone who had two small kids and was six or seven years older than I was made good fit for me at 35 and never married. We had a nice date and she made the move and kissed me at the end, but I wasn't really into it and chalked it up to an "almost, but not quite" encounter.

On that date I had revealed my plans to take a ski trip in a month or so and meet up with some of my family and a friend who owned a ski condo. Ann and I met once more for lunch, more of a friendly encounter than a date, but I made it clear that I thought she was great, but not exactly what I was looking for. I tried to be honest with her, explaining that I was physically attracted to her and that I was trying to be honest with myself about what would really work for both of us in the long term. She understood, but there was definitely an attraction that we both felt and I could tell she thought I was making a bit of a hasty judgement.

A week or two later, Ann sent me an email and we talked about her dire need for a vacation and she asked if I would mind another person on my ski trip. Well, I didn't mind having another person on the trip, especially a hot, sexy woman like Ann, and so a few weeks later we were on the same plane, flying out west to ski. When I went by at 4:30AM to pick Ann up for our flight, I found out that Ann's body was even more smoking hot than I had realized on our one and a half dates. When I showed up at her house to give her a ride and help her with her bags, she was casually dressed in a pair of jeans that clung tightly to every inch of her rock-hard, petite but very round and sexy ass and went down tightly past the knee to show off her runners legs. The jeans ended with a boot-cut flair that showed enough of her mid-heeled black leather boots to know she was one sexy woman. Add to that perfect bottom half, a thin, white silk turtleneck sweater that clung tight to her torso, revealing her perky, perfectly round headlights pointing directly at me from the top of her chest.

It was at that moment that I realized that my new ski buddy had a very sweet pair of perfectly sized, round, prescription tits. Not huge, but the size of large navel orange halves, clinging high on her taut, muscular frame and expertly put there. In the thin sweater and bra, the shape of her rack was definitely too perfect and round to be anything other than the work of a good plastic surgeon. That first day was a hard one to begin a vacation, a very early morning, a long flight, a two hour drive and we still managed to get in a half day of skiing. We quickly followed it up with a group dinner, wine at the table and capped it off with a few drinks at the new microbrewery next door to Jake's. We had fun, a boys ski trip with the exception of Ann and the condo owner's wife. Ann quickly fit in to our group that consisted of my brother and an uncle that was like an older brother to me and the house owners, Dan and Cynthia, who were in their 60s, but fun, energetic people.

What I didn't expect that night was Ann's reaction to alcohol at altitude. She went from fun and happily buzzed with the three of us at the bar, to drunk in the parking lot and then hammered and barfing in the condo a few moments after we got home. I stayed with Ann, first holding her hair so it wouldn't flop in the kitchen sink as she suddenly bolted up from the couch and puked in the kitchen, then I took her downstairs to the guest bathroom and looked after her until most of the worst was over as she drove the porcelain bus from that familiar position on the bathroom floor. I bounced between her prone position down in the barfroom and up in the kitchen to clean the floor and the kitchen sink and a little bit that found it's way onto the carpet.

I took very good care of my sick friend and after she finally stopped puking, I cleaned her up in the sink, had her gargle a little mouthwash and pulled a clean t-shirt of mine over her bra, got her tucked into the double bed next to mine in the room we were sharing at my friend's condo. Then I cleaned the toilet and bathroom floor before going to bed myself.

The next day, Ann bravely got up with the rest of us, had breakfast and went skiing with us, taking a morning lesson and practicing her newly coached turns in the afternoon. The rest of us free-skied all day, veterans of the mountain and all advanced or expert skiers or boarders. My brother, uncle and I met up with the whole crew for lunch, our hosts and Ann having spent the morning on less challenging terrain. Ann was still feeling the impact of the previous night's unfortunate outcome. At lunch we ate big and I had a beer and after skiing, we all had beers. All but Ann, she stuck with water at lunch and at the bar after skiing was done. We wound up back at the condo where we changed into casual clothes and wemt to an italian dinner. Ann looked great in a pair of black leggings tucked into a pair of black ankle boots with four inch heels and a fitted, ribbed turtleneck sweater that well-displayed her perfect rack. I could see how fit she was and understood her decision to get implants. She had perfectly shaped, chiseled legs and a firm, round ass and a tiny, tiny waist. Before she got implants, her low body fat probably resulted in mosquito-bite size tits.

With the implants, her measurements had to be near perfect, a 34C, 20 waist and 32 inch hip with a round, tight, perfect little ass, all packed into a petite, 5'2" body.

We all put on ski jackets and piled into the rental SUV for dinner, an Italian 'family-style' restaurant a few blocks away from Dan and Cynthia's condo. We got back around 10PM, where everyone else said goodnight and turned in, leaving Ann and me on the couch Dan's master suite room was upstairs and had a portal cut into the wall that looked down onto the living room from his computer nook but from his bed, he and his wife couldn't see the room below. Ann and I sat on the couch, watching TV quietly and she moved up against me and touched my arm and looked at me with those big, blue eyes and leaned into me, snuggling close. We sat like that for a while and then she said quietly, nearly in a whisper, how much she appreciated how well I had taken care of her last night when she got sick and how thankful she was that I agreed to let her tag along because she really did need a break from work.

Her little speech was so sincere and heartfelt as she told me how much she appreciated my attending to her when she got sick. She looked so amazing at that moment, so pretty, sweet and sexy and her eyes and face just lit up as she told me how much she appreciated my kindness. I hadn't thought much about it, it was what you did for friends, especially when your friend is puking in your other friend's condo and if you don't make it right, the invitations to come back may not come again. She looked up at me and kissed me on the lips and it just felt so good. I was definitely attracted to her, she had such a pretty face and an absolutely perfect body. She and I began kissing, gentle, soft kisses at first, then more passionate and deep kisses followed and soon we were making out on the couch like sixteen year olds. She kissed so well, I felt the passion and urgency, the hunger, it was definitely lusty and delicious. I moved my hands over her store-bought tits and she moaned in my mouth, letting me know I was free to fondle her round, half-oranges with her hard and pointy nipples on the ends. Man she was squirming and wiggling against me as I keesed her and rubbed her tits and played with her hard, pencil-eraser nipples.

After a good 15 minutes, she broke the kiss and looked up at me and said "I want to kiss you." and I didn't get her meaning, we WERE kissing, weren't we? I looked at her big blue eyes with confusion and she must have sensed it because she repeated "I want to kiss you." and this time she moved her hand and stroked my bulge with her fingers and French-tip fingernails, making it clear what kind of kissing she was wanting to do. My cock grew a full inch bigger and stiffer as my brain processed her suggestion. This hot, sexy MILF wanted to slurp on my pole. My eyes lit up and I nodded, "mmmm, yes." was about all I got out as she felt for my jean button and zipper and lowered the zipper with those sexy, white tipped nails freshly manicured from a salon. I like a woman who has a nice manicure and Ann had small hands, with long, perfectly shaped fingers that ended with acrylic coated nails. They were clear-coated until the tips, with three quarters of an inch of white tip to accent the nails. They were just the right length to be suggestive without being over-the-top or slutty. Her hands looked very sexy as she stroked my bulge. "Mmmm, you're big." she said quietly and with approval as she used her nails to stroke my cock through my underwear before reaching into my pants and grasping my stiff cock with her small hand and clear-coated and buffed nails, pulling my erection over my pushed-down underwear and jeans.

She stroked me with a well-practiced hand, kept her eyes locked on mine and lowered her head to my lap and licked up the shaft to the tip, as if tasting the first pour from a newly opened bottle of wine. She had that hungry look of a girl who loves to suck dick. Once she had a taste and approved the selection, she swirled her tongue around the crown with the confidence of an accomplished fellatrix, never taking her eyes off mine as she ran her tongue around the glans and then planted kisses all over the head and shaft while holding my trunk with her hand. I watched her eyes and face as she quietly and gently sucked on my absolutely rock-hard cock in the condo living room. The thoughts were racing through my head including the realization that my week-long ski roommate had just morphed into my naughty, MILF ski bunny. I just knew from her attitude and her sobriety that this was the beginning of a week's worrh of fun, rather than a one-time deal.

After several minutes of being throughly and expertly "kissed" on the couch just 15 feet from my host's open portal to the living room, I regained my wits about me and gently pulled her head and consequently her sweet lips off my aching cock. She gave me a puzzled look, as if to say, 'I'm giving you a terrific blowjob, what's the problem?' I pointed up to the loft window, where my friend and house owner was sleeping or resting or maybe even standing a few feet back and peering down and watching as my "friend" demonstrated her gratitude for holding her hair as she puked in the sink the night before. She understood quickly, her surprised look fading.

"Let's go downstairs." I said in her ear and she nodded eagerly and let me get my pants up and buttoned, but not zipped, as we headed down to the basement level.

The light was still on behind the other bedroom door where my brother and uncle were bunked, but Ann and i were unconcerned with that as we got to our room, closed the door and Ann pushed my hips back, forcing me to sit on one of the two beds in the small bedroom. She knelt on the floor between the two beds, right in front of me and I grabbed her head with one hand and felt her black, soft hair in my hand as she deftly unbuttoned the silver button keeping my jeans up. I put both of my hands in her soft, long, black hair and she looked up at me to make sure I was watching her.

I was, intently watching her, as she slipped my cock back into her warm, soft mouth as she held the base with her soft hands and wrapped her white-tipped nails around me. I watched her eyes sparkle with lust and excitement as she took me into her mouth and swirled her tongue around and around the tip of my sensitive cock. "This is better. I've been wanting this..." she said, pausing from her task momentarily before working my cock back into her mouth and taking a big, hard suck that was louder than I think she intended, but she didn't let up, bobbing her head up and down on my aching pole as she got onto a rhythm with her mouth. She started sucking on my cock as she bobbed her head up and down on my stick. I reached out and grabbed her perfectly round orbs through her top and felt her steel-hard nipples poking through her bra and ribbed turtleneck top.

She pulled her mouth off my cock long enough to shuck her top off and unclasp her bra, now kneeling naked from the waist up as she got back to slurping my rod. Yes, she had a perfect body with those tits expertly mounted high on her chest. They were perfectly circular in shape and not overfilled. Because she was so skinny, when I grabbed them, I could feel the slight wrinkle of the implant's seam. It was my first feel of 'bolt-ons' and I liked what I saw and felt. They were perfectly sized for her body and they must have been very sensitive because she began moaning and squirming around on her knees as I kneaded her fake headlights in my hands and teased, touched and played with her pointed, hard nipples. I never knew until that moment how hot I found playing with fake tits was. Damn, I loved playing with her tits, the idea that she bought them to be played with and to show off. I was an instant fan of her fake tits, especially because touching them seemed to give her such a jolt down in her pussy.

She paused long enough to look up at me and say, "Its so nice and big, I love how it feels in my mouth." I replied, "It feels amazing, your mouth is soo good baby. I love the way you treat my aching cock." she beamed with pride and put her wet, soft lips back to work on my member. She was quite a talent when it came to sucking my cock, possessing both enthusiasm and fine technique as she gave pleasure to me with her sweet mouth.

Experience and enthusiasm both count when it comes to giving head and Ann was demonstrating her clearly hard-earned experience badge in expert cocksucking technique. Her ex-husband must have done something really dumb, because it was hard to imagine anyone wanting to divorce this orally talented and beautiful, sweet MILF. Besides her obvious talent and enthusiasm for blowing my cock, she was physically amazing. My god, she could have been a fitness model, her abs and obliques were visible along her flat, tight, smooth stomach and a tasteful navel piercing was another pleasant and sexy surprise to me. I touched her tits, then slid a hand down to her tummy, then back up to her round tits and muttered. "Sooo hot, you are perfect.". Referring to her zero bodyfat, hourglass figure. Her petite waist was tiny, 20 or 22 inches around, a spinner, a cheerleader frame that was as trim at 40 as any college-age cheerleader could be. That comment got her even more turned on and she cupped my balls as she went deeper down on my cock, trying to put five or six of my eight inches into her very talented mouth.

I kept a hand in her hair and one on her perfect half-orange sized tits as I concentrated on enjoying the amazing and enthusiastic cock sucking Ann was giving me. She was great at giving head, she knew how to vary the action, slurping on the whole thing, then playing with the helmet and tip, then sucking sideways on the bottom of the shaft and licking it up and down. She worshipped it, someone or several someones in her past had taught her a great deal about giving great, award-winning head and she was acting as if she was being judged in a cocksucking contest. She also loved it, you could just tell she was getting off on pleasing my slightly oversized cock. Her right hand left my cock and went between her legs to rub her nub as she continued to give me a very complete cock-slurping. I let her keep at it for at least fifteen minutes and kept my hands busy in her hair, fondling her tits amd touching her everywhere i could reach with my hands before I pulled her head up by grabbing a handful of her straight black hair and felt her lips slide reluctantly off my cock with a 'pop' before i pulled her higher to kiss her on the lips and pull her onto the bed.

"My turn." I said as I pulled on her black, skintight pants/leggings and slid them over her muscular, round ass. She was easily a size zero or size two dress and all of 5'2" and 105 pounds of solid, sleek muscle and so moving her around on the bed was easy. I got her pants to her knees and then I slipped off her boots and she helped push the leggings down and off while I slid a hand down her tiny, trimmed landing strip and onto her perfectly smooth pussy lips. Mmmm, she kept it baby smooth down there but for the thin, trimmed strip above. Either waxed or shaved, she was ready to sport the tiny bikini in the hottub on this trip, or maybe she anticipated us getting better acquainted. Either way, she had a sweet, smooth pussy to pet and tease with my fingers and I slid my fingers along both outer lips, catching her pussy gently between my fingers. I heard her gasp before I pushed her thighs apart and dove into her wet, swollen pussy, tasting her leaking juices. She was soaking wet, obviously turned on by cocksucking. Her pussy was sugar-sweet and bright pink as I licked her inner folds.

Her body was very responsive, wiggling her hips as I slid my tongue along the fold of her pussy and teased open her puffy lips with the tip of my tongue. She liked being eaten as much as sucking on me and was squirming around on my face and letting out little moans and mews. She was wet and hot, apparently sucking my cock was a big turn on for BOTH of us. She began to turn her body, I think trying to get into a sixty-nine position so she could fill her mouth again with my cock, but I kept her pinned to the bed so I could concentrate on licking and eating her hot, wet, juicy pussy.

I held her hips down with my arms and kept her still as I ate her pussy, licking, sucking, lapping, slurping and eating her until she was grinding on my face and babbling about cumming soon. I like making women go from being in control of their pleasure, to babbling, begging, needy kittens mewing about how good their pussy feels and how they are cumming AGAIN!!! I kept it up, licking, sucking and keeping her hips held down till I felt her jerk her hips hard and spasm and her legs clamped down around my ears. Bingo!

We are now entering Orgasm City, please visit often. Soon after she clamped those thighs, she came hard on my mouth, talking, cursing, begging, moaning and pleading for more. Mmmm, I have a special sweet spot in my heart for women that love talking dirty during sex, and Ann's vocabulary as she came was a string of lusty, needy, dirty talk. Of course, I would hear about that from my brother and my uncle tomorrow but at the moment I had forgotten about everything except this hot Cougar and her sweet, juicy, tasty little pink hole that I was feasting on.