Sitting behind the wheel Dorothy immediately slid over next to me, dress riding high, from my advantage point on the side, glimpsed bare breast. Making it very difficult to concentrating on driving, when my eyes strayed too long on her tits, she'd say watch the road. At times she'd emphasize the words by biting my shoulder, which didn't help any; just another distraction to contend with.

Arriving at our destination thankfully without incident, parking was minimal curbside almost a block away. Walking to the house she snuggled in close; arm around her shoulder was surprised when allowed to fondle her breast. Right there on the street, under the lights, my dick once again throbbing for what seemed like the hundredth time.

We made it to the front landing, telling her I needed a moment. Her look was predatory, now fully understanding the term "Cougar" Reaching down stroking me, told me that's the point. Without thinking my hands went down her back, cupped one side of her ass, and lifted her leg, and then our world became crowded.

The door swung open, without hesitation Dorothy said to the lady "No telling what you would have seen in a few minutes" Being a man I know how much trash we talk about girls, but never in my life been blatantly talked about within my hearing. The woman said "Dam girl, when you started robbing the cradle?" After a while just started ignoring the comments, coming from women 30 and 40 yrs. older than me, thinking maybe they couldn't help it.

Before I go further need to try to convey the sights witnessed of the guest at first glance. You have to realize never really believed this lifestyle existed or was real. Most the women were between the ages of 35, and met one woman claiming to be 72. Funny thing was you could almost put an age on a woman by her attire. 35 to about 48 most wore reviling dresses, the acceptable style without bras or panties. I did see one woman, early 30s modestly dressed and looking vaguely uncomfortable, but as the wine and evening progressed, modesty fled along with her bra.
Second stage was around 50 to 60 the preferred dress was transparent, unbelievable sheer and tiny panties. Most kept tightly trimmed bushes, rarely did you actually see a bald one.

Lastly what I refer to as the Social-security babes, I use that term with great affection. These ladies are over sexed; refusing to be put out to pasture their desire is just to be fxxked one more time. They had no shame, many wearing black see-though nothing underneath, most sporting thick greying bushes.

The men for the most part were early 20s to mid-30s, classifying them in one of 2 groups. Like me many were there for the sheer joy of being in the company of Milfs, as we find them breathtakingly erotic. The others had the attitude, what's in it for them gifts, money or whatever. The last bunch that that comprised the party, both fascinated, and puzzled me.

Those were the married couples, most the woman being in late 40s, the husbands late 50s. The wives are very flirtatious, always flashing tits, or pussy; husbands mostly stand off and watch in groups. The people there were highly educated professionals, Dorothy being a lawyer. The baulk of the group needed a discrete place to fulfill their fetishes, and fantasies, and the party provides the outlet. The majority of women would enter wearing coats, hiding their provocative wear in public. Other much like Dorothy, proud of the fact she was a Cougar, discretion fleeing once in a new city. They get off flaunting their sexuality in public, thrilled by the commotion it causes being with a much younger man.

They were a close net social-club, holding parties once a month, hosted for the most part by the Social-security babes. Many of the members had blocked profiles for privacy, a couple or woman applied for membership, 3 S-S babes voted in each new applicant, and also exiled an existing member. Single men couldn't apply, but needed an invite, or accompany a member to a party. Membership was $100 a month, used for the soul purpose of securing a block of cabins on a cruise ship getaway once a year. Dorothy explained this all to me Sunday morning, and found myself concerned; $29.99 for the site, there's no way can afford $100 on top of that. Told Dorothy wasn't sure if wanted to join at this time, kissing me she said "Our new little cubs are waved of fees"

Dorothy was amazing, if across the room chatting with friends she'd see me looking; out of the blue she might pop out a tit blowing me a kiss. At other times she'd be so dam frustrating, her actions so unpredictable. I was sitting on the couch, with like three people, watching this married woman moving in my way.

She plops her ass down shimmy it in, forcing the others to move. She starts informing me of the nasty things she'd enjoy doing to me. Her husband comes up, my 1st thought is "O shit" but he just hands me a drink saying "Do you think she'd be a great piece of ass?" How do you respond to that, again I've read about situations like this, but it doesn't fully prepare you? I see Dorothy heading our way, again the unexpected.

This is my 1st real date with Dorothy, so don't have a good feel for her nature; whether she's prone to jealousy, or anger. She hikes her dress up a little and straddles me, her knee forcing the woman to slide over making some poor bastard on the end get up for lack of room. She places an arm around my neck, her boobs fall out, then grinds her pussy against my dick trapped in jeans. Without missing a beat, her free hand extracts the drink from my fingers, saying "My baby boy's old enough to fxxk, but not to drink" handing it back to the man. Dorothy nibbled on my neck, laughing she got up saying, "Hope I didn't stain your jeans much?" They all looked; the lady asked "Really how old are you?" My response, "Not old enough to drink" I excused myself to find a bathroom.

By my dick has been in a state of hardness for the last 5 hrs. We've been here a couple, and everywhere you look see tit, and pussy leaving me with a perpetual erection, and discomfort. Don't get me wrong I've seen plenty, only this is all older, and so much giving me a sensory overload. Trying to urinate with a hard-on is by no means a simple task. So here I am swollen dick in hand, when one of the Social-Security babes walks in. She actually asked if I needed a hand. After she leaves, finished the task at hand, no pun intended. Returning to the party, the first thing I see is Dorothy, the S-S babe talking and giggling.

I'd be very amiss if I didn't include this. The house was huge, in the sitting room we occupied; the back wall was comprised of all glass in a circular shape leading to the deck, and back yard though an enormous glass French door. I'm looking out seeing someone bent over a table skirt hiked up being pounded from behind. Next thing I know Dorothy's has her arms wrapped around me, asking if found something interesting. My focus was so intense I failed to realize others had joined me to watch. Dorothy told me "Cougar in training" I wasn't sure what she meant, so asked; her explanation was a woman like a man needs coaching sometimes. She's been on the site for a while asking questions, not sure how to approach young men. The hostess invited her, sent her profile to a few, and then invited a confidant young man to hit on her.

Still watch the couple outside told her "So you manipulated her" her explanation made sense telling me I was a "Cub in training" I bristled a little at that statement, but like a lawyer she built her defense. Asking me questions like "How many Cougars did I contact?" (0) "How many profiles did I look at?" (Estimated around 200) She told me some people need it to attain their goal, like her, or me, so I realized she was right.

My 1st sight of this woman was sitting on the couch in a modest wrap dress legs crossed hands on knees, later in a corner making out with a man; then being bent over a table. Once finished, Dorothy pulled me away from the window telling me to watch and learn. The woman stood starting to rearrange her clothing; the man hugged her tight, taking her bra, and panties tossing them into the darkness of the yard. What really impressive, was when he convinced her to leave her dress untied, giving flashes of tit. With an air of satisfaction "See she wanted to be manipulated, now your turn"

Taking me by the hand lead me to the bathroom, unzipped my jean getting ahold of my dick stroking it, asking "If I wanted to go back to the hotel and fxxk?" Whispering all the nasty things she wanted to do, then just stopped and told me to put my dick away. She once again got that predatory look, instructing me to find our hostess apologize for leaving early saying "My Cougar wants to fuck" then turned leaving.

In the other room, Dorothy's chatting with some people nods the ladies direction, and then wiggling her hands in the gesture to go on. I'm standing discretely by the group of guest while they talk, mentally hoping they'd leave, and then she gives me that predator look saying "Boy what's on your mind?" I ask her if could have a moment of her time her response "We're all friends here right?" This lady has a loud booming voice, embarrassed I mumble, the lady says "What?" then to make matters worse, she raises her hands shouting for quiet saying "Our new little cub has an announcement he wishes to make."

I could have almost strangled her, and then Dorothy came up asking "So what's my cute cubs' announcement?" I now comprehended the true nature of their manipulation, though the course of the evening watched my language, always spoken respectful to each person regardless of how I was approached. So I swallowed my embarrassment saying "My Cougar wants to go fuck" I felt my ears burn, everyone laughed but at the discomfort it took saying that, not directed at me.

The hostess then addressed Dorothy saying "Since your cub has failed to post his dick in the profile, we're wondering if you'd be able to entice him to?" That was too much, and I think Dorothy understood that, so to help me out said "Better yet, I'll post a picture of me holding it later in the week"

At that point couldn't leave fast enough, Dorothy took her time kissing cheeks in farewell, ladies gave me goodbye hugs pressing all sizes and shape of breast to my chest. Some even expresses lewd comments of what Dorothy was going to do, or what I should do. Never did I expect the sound of a door closing to be such sweet music to my ears.

The Party
Sitting behind the wheel Dorothy immediately slid over next to me, dress riding high, from my advantage point on the side, glimpsed bare breast. Making it very difficult to concentrating on driving, when my eyes strayed too long on her tits, she'd say watch the road. At times she'd emphasize the words by biting my shoulder, which didn't help any; just another distraction to contend with.

Arriving at our destination thankfully without incident, parking was minimal curbside almost a block away. Walking to the house she snuggled in close; arm around her shoulder was surprised when allowed to fondle her breast. Right there on the street, under the lights, my dick once again throbbing for what seemed like the hundredth time.

We made it to the front landing, telling her I needed a moment. Her look was predatory, now fully understanding the term "Cougar" Reaching down stroking me, told me that's the point. Without thinking my hands went down her back, cupped one side of her ass, and lifted her leg, and then our world became crowded.

The door swung open, without hesitation Dorothy said to the lady "No telling what you would have seen in a few minutes" Being a man I know how much trash we talk about girls, but never in my life been blatantly talked about within my hearing. The woman said "Dam girl, when you started robbing the cradle?" After a while just started ignoring the comments, coming from women 30 and 40 yrs. older than me, thinking maybe they couldn't help it.

Before I go further need to try to convey the sights witnessed of the guest at first glance. You have to realize never really believed this lifestyle existed or was real. Most the women were between the ages of 35, and met one woman claiming to be 72. Funny thing was you could almost put an age on a woman by her attire. 35 to about 48 most wore reviling dresses, the acceptable style without bras or panties. I did see one woman, early 30s modestly dressed and looking vaguely uncomfortable, but as the wine and evening progressed, modesty fled along with her bra.
Second stage was around 50 to 60 the preferred dress was transparent, unbelievable sheer and tiny panties. Most kept tightly trimmed bushes, rarely did you actually see a bald one.

Lastly what I refer to as the Social-security babes, I use that term with great affection. These ladies are over sexed; refusing to be put out to pasture their desire is just to be fxxked one more time. They had no shame, many wearing black see-though nothing underneath, most sporting thick greying bushes.

The men for the most part were early 20s to mid-30s, classifying them in one of 2 groups. Like me many were there for the sheer joy of being in the company of Milfs, as we find them breathtakingly erotic. The others had the attitude, what's in it for them gifts, money or whatever. The last bunch that that comprised the party, both fascinated, and puzzled me.

Those were the married couples, most the woman being in late 40s, the husbands late 50s. The wives are very flirtatious, always flashing tits, or pussy; husbands mostly stand off and watch in groups. The people there were highly educated professionals, Dorothy being a lawyer. The baulk of the group needed a discrete place to fulfill their fetishes, and fantasies, and the party provides the outlet. The majority of women would enter wearing coats, hiding their provocative wear in public. Other much like Dorothy, proud of the fact she was a Cougar, discretion fleeing once in a new city. They get off flaunting their sexuality in public, thrilled by the commotion it causes being with a much younger man.

They were a close net social-club, holding parties once a month, hosted for the most part by the Social-security babes. Many of the members had blocked profiles for privacy, a couple or woman applied for membership, 3 S-S babes voted in each new applicant, and also exiled an existing member. Single men couldn't apply, but needed an invite, or accompany a member to a party. Membership was $100 a month, used for the soul purpose of securing a block of cabins on a cruise ship getaway once a year. Dorothy explained this all to me Sunday morning, and found myself concerned; $29.99 for the site, there's no way can afford $100 on top of that. Told Dorothy wasn't sure if wanted to join at this time, kissing me she said "Our new little cubs are waved of fees"

Dorothy was amazing, if across the room chatting with friends she'd see me looking; out of the blue she might pop out a tit blowing me a kiss. At other times she'd be so dam frustrating, her actions so unpredictable. I was sitting on the couch, with like three people, watching this married woman moving in my way.

She plops her ass down shimmy it in, forcing the others to move. She starts informing me of the nasty things she'd enjoy doing to me. Her husband comes up, my 1st thought is "O shit" but he just hands me a drink saying "Do you think she'd be a great piece of ass?" How do you respond to that, again I've read about situations like this, but it doesn't fully prepare you? I see Dorothy heading our way, again the unexpected.

This is my 1st real date with Dorothy, so don't have a good feel for her nature; whether she's prone to jealousy, or anger. She hikes her dress up a little and straddles me, her knee forcing the woman to slide over making some poor bastard on the end get up for lack of room. She places an arm around my neck, her boobs fall out, then grinds her pussy against my dick trapped in jeans. Without missing a beat, her free hand extracts the drink from my fingers, saying "My baby boy's old enough to fxxk, but not to drink" handing it back to the man. Dorothy nibbled on my neck, laughing she got up saying, "Hope I didn't stain your jeans much?" They all looked; the lady asked "Really how old are you?" My response, "Not old enough to drink" I excused myself to find a bathroom.

By my dick has been in a state of hardness for the last 5 hrs. We've been here a couple, and everywhere you look see tit, and pussy leaving me with a perpetual erection, and discomfort. Don't get me wrong I've seen plenty, only this is all older, and so much giving me a sensory overload. Trying to urinate with a hard-on is by no means a simple task. So here I am swollen dick in hand, when one of the Social-Security babes walks in. She actually asked if I needed a hand. After she leaves, finished the task at hand, no pun intended. Returning to the party, the first thing I see is Dorothy, the S-S babe talking and giggling.

I'd be very amiss if I didn't include this. The house was huge, in the sitting room we occupied; the back wall was comprised of all glass in a circular shape leading to the deck, and back yard though an enormous glass French door. I'm looking out seeing someone bent over a table skirt hiked up being pounded from behind. Next thing I know Dorothy's has her arms wrapped around me, asking if found something interesting. My focus was so intense I failed to realize others had joined me to watch. Dorothy told me "Cougar in training" I wasn't sure what she meant, so asked; her explanation was a woman like a man needs coaching sometimes. She's been on the site for a while asking questions, not sure how to approach young men. The hostess invited her, sent her profile to a few, and then invited a confidant young man to hit on her.

Still watch the couple outside told her "So you manipulated her" her explanation made sense telling me I was a "Cub in training" I bristled a little at that statement, but like a lawyer she built her defense. Asking me questions like "How many Cougars did I contact?" (0) "How many profiles did I look at?" (Estimated around 200) She told me some people need it to attain their goal, like her, or me, so I realized she was right.

My 1st sight of this woman was sitting on the couch in a modest wrap dress legs crossed hands on knees, later in a corner making out with a man; then being bent over a table. Once finished, Dorothy pulled me away from the window telling me to watch and learn. The woman stood starting to rearrange her clothing; the man hugged her tight, taking her bra, and panties tossing them into the darkness of the yard. What really impressive, was when he convinced her to leave her dress untied, giving flashes of tit. With an air of satisfaction "See she wanted to be manipulated, now your turn"

Taking me by the hand lead me to the bathroom, unzipped my jean getting ahold of my dick stroking it, asking "If I wanted to go back to the hotel and fxxk?" Whispering all the nasty things she wanted to do, then just stopped and told me to put my dick away. She once again got that predatory look, instructing me to find our hostess apologize for leaving early saying "My Cougar wants to fuck" then turned leaving.

In the other room, Dorothy's chatting with some people nods the ladies direction, and then wiggling her hands in the gesture to go on. I'm standing discretely by the group of guest while they talk, mentally hoping they'd leave, and then she gives me that predator look saying "Boy what's on your mind?" I ask her if could have a moment of her time her response "We're all friends here right?" This lady has a loud booming voice, embarrassed I mumble, the lady says "What?" then to make matters worse, she raises her hands shouting for quiet saying "Our new little cub has an announcement he wishes to make."

I could have almost strangled her, and then Dorothy came up asking "So what's my cute cubs' announcement?" I now comprehended the true nature of their manipulation, though the course of the evening watched my language, always spoken respectful to each person regardless of how I was approached. So I swallowed my embarrassment saying "My Cougar wants to go fuck" I felt my ears burn, everyone laughed but at the discomfort it took saying that, not directed at me.

The hostess then addressed Dorothy saying "Since your cub has failed to post his dick in the profile, we're wondering if you'd be able to entice him to?" That was too much, and I think Dorothy understood that, so to help me out said "Better yet, I'll post a picture of me holding it later in the week"

At that point couldn't leave fast enough, Dorothy took her time kissing cheeks in farewell, ladies gave me goodbye hugs pressing all sizes and shape of breast to my chest. Some even expresses lewd comments of what Dorothy was going to do, or what I should do. Never did I expect the sound of a door closing to be such sweet music to my ears.

Saturday morning reared its ugly head, flooding me with anxiety, and anticipation on the unknown. Up to this point the oldest female I've ever dated, was a sophomore collage girl, who was my escort to the Senior Prom.

My anxiety wasn't based on fear, but the idea that this was trial and air situation. I looked at profiles of other dudes on the site; they averaged between 22, and 36, so that made me the youngest validated member. It's a good thing, which enticed a lot of Cougars to contact me, but still left me unsure how to interact.

We were heading to Dallas, a few hours to my place then another 3 hour drive to our destination. Dorothy insisted picking me up at my apartment, then driving the reminder of the way. I'm waiting out front, when she pulls up around 5pm very prompt she gets out informing she needs to use the restroom.

This is what I really wanted to avoid, my 1st apartment sparsely furnished with 3rd hand furniture from a second hand store. In my apt. she uses the word "This is Quaint" Then ever so sweetly asked "Is that what you're wearing?" Irritation rear its ugly head, but was able swallowed it down. She was wearing jeans, and a light blue low cut sweater. It showed the wonderful flow of cleavage, but I was expecting a bra-less dress showing lots of flesh; now she was concerned with what I was wearing. The last one to use them terms was mom, so found it a little creepy.

Describing myself honestly I'm 5'9" eating heathy, run and workout with weights, I'm no bodybuilder, but my cuts emphasized with a slender frame. Using a scale of one to ten, I conceder myself around 6, a touch above average.

Dorothy asked if had any jeans that were tighter, then felt my bisects, went into my bedroom to look for a different shirt. Not knowing how to respond just followed her. While I was changing jeans she started digging for shirts, finding 6 she like, saying she'll decide later on which one; after approval of my jeans.

Arriving in Dallas Dorothy pulled into the drive of the Rosewood Mansion, I cringed, my budget being more on the line of Motel6, and started thinking how long was going to be paying on my credit-card. A valet rushed out to open her door, another materialized from thin air, with a cart to ship belongings. Tips? Had a little cash, but now started wondering where an ATM was located.

Once we past the threshold of the hotel, her demeanor changed, it was kind of disarming in a good way. She took me by the arm pressing close, as we walked to the registry desk giving her name, saying we had a reservation. Dorothy signed the required papers, I pulled out my wallet, smiling she kissed my cheek saying "Isn't he so cute" then informing me it was already taken care of. I'll admit did get a little embarrassed.

In the room wanted to have sex right then and there, I believe she knows that, looking at her phone, calmly states after we have dinner, and we'll be late for the party. Dorothy took a small travel case heading into the bathroom, saying over her shoulder "The garment bag holds a few outfits pick the one I like."

Once the door closed, I jumped out of the chair like a kid heading to the tree on Christmas. Inside was 4 dresses, arranged carefully everything included down to panties.

The 1st was a red Swede halter top, with matching long skirt that had a split up the side; nice but...... to much pantie! Next one a pink tube top mini, matching pink thongs, OK but.... On to a dark blue halter mini-dress, short and sweet, completed with lacey G-string panties. This was defiantly what I thought was what Cougars should wear; my dick was hard imaging her in it. I had pretty much made my mind up until saw the last dress; it was something from the promise land. Black short and thin, not what you'd call transparent, but close. I learned later it was called a drape dress, with gathering sides to draw it up. I looked in the bag searching, but didn't find the missing panties.

The door opened Dorothy was wrapped in a towel smiling at my request, later after a little wine, she confessed to manipulating me with panties; so I never really had a choice. Waiting for her return was agonizing! When she next appeared, the sight of her made me think; I could die, and leave a happy man, well almost.

Dorothy's breast had just a little sag, nipples still pointing up, but the way the dress draped over them emphasized their size, the top of her naval was peeking out as she moved. She had drawn the stings up creating a small v on both sides. When she spun for my inspection you could see little flashes of nipple. It was backless save for tiny silver ringlets to keep her ass from being exposed. Jewelry was kept simple, large silver hoops in the ears being accented with her dark auburn hair. Around her neck was this silver wisp of a neckless, with a small delicate pendant in the image of a Cougar paw. Dorothy had bright red lipstick on, her eyes were done it a fashion of Cleopatra asked if "Is your Cougar slutty enough" Then her actions distressed me again.

Walking up to me, she pressed her fingers against me, slowly unbuttoning my shirt to the waist, untucking the tails from my jeans. Her hand lingered on my chest, with a small sigh, just up and stopped wanting me to let her see which shirt she wanted. She encouraged me to wear the blue muscle shirt.

I'm now living the dream; events become surreal like I'm participating in a movie watching each frame unfold. Dorothy seemed to make a radical metamorphosis, into this woman completely different woman I met in the coffee shop. Her voice took on a husky quality, over laid by that sugary sound.

In the restaurant everyone stared as we walked hand in hand, when I pulled her chair out, I'll admit my fingers lingered a bit too long on her bare back, which she seemed not to mind. She ordered wine for herself and a coke for me, then looked me over the rim with Egyptian styled eyes. Every now and a breast would fall free, and Dorothy without haste confined it once more. At one point during the meal, she slipped her shoe off tracing my dick with her toe. I almost choked on the food being chewing.

Dorothy talked about the couples around us, who was getting some, and naturally who wasn't. She continued that most men in here uses the little blue pill, that's why most the women are staring, and many of the men wish their wives tits would pop out now and then.

One thing I owe to mom is; she instilled me with gentlemanly etiquette. When Dorothy informed me she needs to powder her nose, it cloaked me in a state of conflict, being aroused. She sat calmly waiting knowing eventually I'd rise out of the chair with great embarrassment to help her up. She looked at my crotch, in that husky voice said "Someone's excited" making matters worse, gave me and the table next to us a pussy shot. Hurrying back to my seat watched her move to the restroom not a care in the world. The thing that struck me most was watching the peoples following her movement, a few men receiving frosty stares from their companions. What surprised me the most is, I received a few nots of approval.

Leaving the restaurant, eyes burning into my back, she whispered "You drive"

 I’m attempting to explain this as it unfolds, unfortunately find my writing skills are less to be desired. This is defiantly a new experience!

I heard from Dorothy the following Tuesday, and the first thing she asked me, “Why wasn’t my profile changed to being her cub?” This is getting a little crazy, so went to her profile, and sure enough, in her space for relationship was my acct# and name, under that she wrote, “My sexy little cub” I changed mine, satisfying her.

She asked if I had plans for Saturday night, if so cancel them. Then informed me what I should wear, like I was 2 or something. A black suit and tie for Christ sakes, the last time I wore one of them was visiting a dead person. I told her didn’t have one, Dorothy offered to buy me one, but made it real clear I’m not kept, nor will ever b. After haggling a bit, we found something I owned acceptable.

Paybacks are a bitch! If I’m a cub, that makes her a Cougar, and I’ve been chewing over this all week. So I asked her if, she was going to dress like one. We’re talking on the phone, she laughs asking what I think a cougar should wear. I’m comfortable now, so said the 1st thing that pops in my head, “Something that shows lots of skin”

All I really know of Cougars if what I’ve either read, or images looked at. To be frank, the ones seem on (ImageFab) show scantily dressed Milf running around public. I’ve never seen it, so figured it’s more of a fantasy concoction.

One thing I did realize about Dorothy is, she was interested in how many messages I received, and if received any invites from private clubs. Her response to the messages, gave me an inside clue to the mentality of a Cougar. It pleased her that others wanted what she felt she had, yet agitated her, that they ignored the stasis of my relationship.

The way I’m beginning to understand the site, the intention was for older woman to meet younger men, or vice-versa. They have private groups, or clubs that meets in local areas to have parties and get together at a host home. Privacy I suppose. Our 1st date will be held in one such home event.

To be honest have no idea what to expect, or the outcome. This is almost like a Reality show, I’m being forced to wait for the finally, hopefully I won’t be disappointed!