Who's Being Pursued? Pt. 02

In Part 1 we met Regina and Michael and followed them through their first sexual encounters. Let's start off Part 2 with a bit of background this sexy woman

--------

Her name is Regina and she is a recovering nymphomaniac. Is there really such a thing as a recovering nymphomaniac, or are they like alcoholics? Always one drink, or one sexual act, away from relapsing.

Her hair was flaxen blonde in her younger years but by her forties it had darkened to more of an ash blonde. For years she had battled the darkening but now she'd given up. Streaks of silver and white give her hair the look of expensive highlights. She thinks it's quite attractive and men seem to agree.

Her eyes are a piercing blue, they'd always been that way even as a baby. It's as if she's looking through you, or maybe you're looking through her eyes into another dimension. Look too long and you might loose yourself in her gaze. Then there's her smile. She had spent a lot on dental work over the years, both out of necessity and vanity. Now her smile appears almost perfect. Pearly white and lined up in a row like the white keys on a piano keyboard. When she smiles at you, and if you're a good looking man she will smile at you, it grabs your attention and it's hard to look away. You'll think about her smile, and her eyes, for days.

Her face belies her age. There are the subtle hints of aging, some wrinkling around the eyes, a slight sag in her eyelids, a few age spots now faded thanks to modern facial care products. The ravages of time have so far passed her by.

If you can get beyond being captivated by her face then you'll find an amazing body waiting for you to feast your eyes upon. At 68 years of age she's in incredible shape, and she knows it. She uses her looks and her manner of dress to get pretty much any man she wants. She stands about 5'4" barefoot but she's usually in heels when she's with a man, or pursuing one. She has the perkiest breasts of any woman her age thanks to a skilled plastic surgeon, B-cups that that bounce as she walks. One former husband used to say that her nipples point towards heaven. When they get excited you can hang a shirt off them, the proof is in one of her porn videos, yes porn videos. More on that in a bit. She dresses to thrill, body conscious clothes, heels, professional bordering on provocative. If she's out running errands she's typically in sneakers, walks with a bounce and rarely wears a bra. She always projects an air of confidence.

She's always had a high sex drive and was pretty wild in her younger years. In school she always popular with the boys, and it was not solely due to her personality. Even in elementary school the boys were always hanging around. In high school it was one boyfriend after another and following that it was one husband after another. Her daddy once told her, "Regina, you're hornier than a three-peckered Billy goat". She's been married three times but never had kids, not that she and her first husband didn't try but turns out that she can't. Since she would never have a child of her own she'd had surgery to make sure of it. She found sex without the risk of pregnancy to be amazingly liberating. Her first two marriages ended when her husbands couldn't keep up with her sexual needs. Invariably she took on lovers but was always open about it. One husband left her immediately, another agreed to be her cuckold if he could watch occasionally. That marriage lasted about another year before he realized she was spending more time with her various lovers than she was with him and that her lovers were showering her with gifts that he could never match.

Her last husband was into bondage, serious bondage, rope play, suspension, ball gags, blindfolds, stockades, collars, and pain. He was the one who got her into porn as an actress. She always played the slutty blonde MILF that got tied up and gang banged by guys with huge dicks, often black guys. She enjoyed the sex but the stop-go-repeat nature of filming it led to a lot of sexual frustration. That was her least favorite part of the porn industry.

Then her family found out about the porn. A friend of a friend of her sister saw one of the videos online. Well, that friend told her sister and then she told their momma. Momma she was livid, she told her, "Gina, if you had as many things sticking out of you as you've had stuck in you over the years you'd look like a porcupine. You're nothing but a common tramp and I'm ashamed to say you're my child". That hurt Regina a lot coming from her beloved momma, the woman that gave her life. She begged her momma and her sister not to tell her daddy, the first man to put her on a pedestal and still the only man she'd ever been truly loved by. They agreed under momma's condition that she quit doing porn. When she told her husband that she was through doing the videos, he got angry at first, then he tried to lure her to continue doing the videos with a way to make more money by doing some sick stuff that is a real niche market but very lucrative. When she refused, he left her.

That whole experience was a real wake up call and she went through a period of radical change. She's been single now for twenty years and never been happier. With the help of a therapist she realized that she has hypersexuality disorder, what used to be called nymphomania or sexual addiction. Though she no longer engages in the destructive behaviors characteristic of her condition, and the depression that typically accompanies it is under control, she does still have a high sex drive. She has a few close female friends that know about her past, in addition to therapy they are her support system.

Her daddy passed a few years after the last failed marriage. He never found out about her brief foray into porn videos. She was his Gina to the end. He owned an Irish Pub in town, it had been his since before he met his wife, and before that it was his daddy's. When he passed away the pub became Regina's. She was the only one in the family that knew anything about running it, or had any interest in it. She'd worked there when young and her daddy taught her all aspects of running it, he kept her involved ever since as if she was his partner. She had picked up many a man there in her younger days, guys seem to feel comfortable hitting on an attractive bartender. She received many tips, both cash and cock, by flirting across the bar.

Nowadays she's much more selective about the men she beds. No more prowling for men in clubs and bars every weekend for a one night rush of sexual satisfaction. Most of her sexual relations now are long term, she finds men that she enjoys sex with, men who give her a measure of relief from her constant craving of cock, and keeps them around. But a girl needs some variety so a one night stand is not out of the question. If you're a normal guy and she sets her sights on bedding you there's little chance that you won't succumb to her advances. She will have her way with you. If you're attracted to her and make a move, thinking you are the pursuer, what's probably happened in reality is she's tricked you into thinking you're in charge. For example, her latest pursuit is Michael, he's a sexy man only eight years younger than her. He's a widower and she thought his experience and skill would be a plus for giving her satisfaction. Maybe he'd be open to exploring some kinkier aspects of her needs. "You can't trust just any man to tie you up and take charge of you," she would say. She's had young guys get carried away, inflicting real pain, and after all, a woman her age has to be cautious.

She'd known for a while that Michael had a thing for her. He was always smiling, looking into her eyes, watching her ass as she escorted him around when he came to the hospital for testing. She was aware of this and did everything she could, short of undressing, to encourage him. She was prepared the day he finally got up the nerve to approach her. She'd been about to proposition him herself. He asked to buy her lunch but she wanted an easier route to her bed so she suggested dinner. And she suggested the pub so he'd be on her turf. At the right time that night she pounced and he ended up in her bed.

He is a fantastic lover, skilled with his cock and tongue, aggressive but so gentle. He is just what she needs for some bondage play. And his cock! It's the biggest she's had in a while, a fat cock that spreads her wide. Their first night together she learned he'd been fantasizing about her. She knew she'd be able to keep him around for a while, and after she made him cum he was hooked. That first night he did something she'd not had any other man do to her, at least intentionally. He edged her, taking her to the point of cumming and then backing off several times. Now she was hooked on Michael. He also has a kink of his own, after filling her with cum he licked her pussy clean. She so enjoyed fucking him that she decided that she would make his fantasy come true. She also decided that he was the perfect partner for some light bondage play.

Their second night together she introduced him to light bondage. She had him hook her to a spreader bar while standing and put a collar and blindfold on her. Her last husband would have inflicted pain but she gave Michael some fruit and sweets to use, something she'd never done before and wasn't sure how he would react. That night was incredibly satisfying. She'd never experienced anything like what he did to her. Michael seemed excited by the situation that night and made sure they both had a fantastic experience. By the time he finished with her she was covered in a sheen of fruit juice, condensed milk, and saliva from the tongue bath he gave her, and she was dripping cum. The next morning she awoke next to him in bed with a sore pussy, not remembering how she got there. She decided Michael is definitely her man when she feels like a little bondage.

One of my other men is Grant. He's about 30, average guy all around including his cock but damn does he have stamina. When she needs a good fucking in every hole he's her go to. He's still able to cum twice an evening. He's a local pediatrician who's divorced, his wife wanted him around more often but he's dedicated to his work. She helps him relieve the stress with no commitments.

Michael's fantasy of her involves sex on an exam table. Her first thought when planning to make it come true was that they'd do it in a room at the hospital where she works, but Michael was concerned that she'd lose her job if they got caught. Then she realized that she had the perfect spot available to her, Grant's office! She approached Grant about it after a marathon Saturday sex session where she'd had him in her mouth, cunt and ass. He agreed to let her use one of his exam rooms after business hours on the condition that he got to put his cock in her cum filled pussy. Sloppy seconds, how could she refuse! She arranged with Michael and gave him his fantasy of bending her over an exam table and watching his cum drip into her panties. When he left the exam room he had a huge grin on his face and she definitely enjoyed the fantasy as well, hard and fast, almost anonymous sex.

So, enough about Regina's background and her recent sexual encounters, for now. Let's pick it up after Michael left her panting and dripping, bent over the table in one of Grant's exam rooms.

--------

Grant was in his office that night doing paperwork, waiting until Michael left so he could come in and plunder my just fucked cunt. Hearing the door close he waited until Michael drove away then went and locked the exterior door, I waited for him, still bent over the exam table.

"Good evening Regina, what seems to be the issue today," he asked as he entered the room and stepped over to the counter. I heard him snap on a pair of exam gloves.

"Well Doc, as you can see, I have this leakage."

He rolled a stool over and sat behind me, "well, let's take a look here." He pulled out the bottom step on the table and told me to step up and bend over all the way. I did, and now my ass was way in the air and my tits on the table, putting my dripping cunt at the same level as his face.

"Hmm, that's quite some leakage, it appears to be a man's cum," he said as he probed my labia with his fingers. "I'm going to insert a finger or two and try to find how much of this is in you."

He slid two fingers into my dripping, swollen cunt, I moaned. Damn that felt good. He began working his fingers in and out, curling them and rotating his hand, causing more of Michael's cum to drip into my panties. I was moaning and breathing heavy, then he hit my G-spot and I came on his fingers, my legs quivered and I nearly collapsed.

"Is it bad Doc? Is there a lot left in me?" I asked, breathless from my orgasm.

"I think I've cleared most of it here but I want to check your anus, make sure there's nothing there that might start leaking later," he said very professionally and then he pulled his fingers out of my cunt and slid one up my ass. It was covered in cum and slid in very easily. He put the second back into my cunt.

"Ooooh, yeessss," I moaned. He worked his two fingers in and out, pleasuring me. Using his other hand he rubbed my clit. I moaned and quivered and came for him again.

"Hmm, your anus is clear but I'm still seeing leakage from your vagina. I need you to change positions and I think I need a larger probe," he said as he removed his gloves and tossed them into the biohazard bin.

He had me stand and remove my pants while he adjusted the table to a sitting position and installed the stirrups. I sat on the table for him and placed my feet in the stirrups. He dropped his pants and stepped between my parted legs.

"This might take a while," he said. He took his time rubbing the head of his cock between my cum-soaked cunt lips. Several times he rubbed the head on my clit and I could see it. His tip was covered in Michael's cum and he was enjoying it, his head was laid back, his eyes were closed, and he was softly moaning "yes, oh fuck yes." His entire cock was soon covered in Michael's cum and he finally slid it into me.

"Take your time Doc," I moaned, "I need to have this issue addressed properly." I felt like such a slut, just like back in the days when I did those porn videos, multiple cocks one after another, fucking me good. Grant fucked me nice and slow for several minutes and I could feel more of Michael's cum getting pumped out and flowing over my asshole. Since I was sitting up I could see his shaft, it glistened from a combination of my wetness and Michaels cum. A thought occurred to me, maybe I could get these guys to take me together, a threesome, and with dp! One in my cunt, the other in my ass, it has been a long time since I've done that. Michael had already taken me with a butt plug and Grant was enjoying wading into Michael's cum. I filed that away for future consideration.

"Oh that probe feels good Doc, take your time and do this right, I don't mind at all," I said with a groan.

"I'd better check our progress," he said as he pulled out and stepped back. "Well, you're very red and swollen, but it seems the leakage has stopped, except now your anus is showing signs of leakage. I'm not sure where that's coming from so I'd better double check. He stepped back between my legs and gripping his cock, he placed it against my wet asshole and told me to relax. With my own fluids and Michael's cum as lubricant he slowly filled my ass with his cum covered cock.

I gasped as the tip forced me open and split my sphincter, then I moaned as I relaxed totally and took him in. "I appreciate you being so thorough," I groaned. I laid my head back and enjoyed the feeling of having my ass full of him. Just like with my cunt he fucked me slowly. Unlike Michael's fantasy where we had to hurry or be caught Grant was taking his time with me. I regretted not sucking on his cock before he put it in my ass, I could have had all my pleasure holes used this evening.

Eventually he put a finger on my clit and did little circles and soon I was cumming for him again. My sphincter gripped his cock and he drove deep into my ass as he moaned in pleasure. I felt his cock spasm as he dumped a load of cum in me and I thought great, now I'm going to leak from both holes!'

Grant pulled his softening cock out of my ass and sat on the stool again. "Well Regina, I think I might have made matters worse. You're probably going to leak heavily, very heavily, from your anus as well. There are some pre-moistened disposable towels there on the counter, why don't you clean up and I'll see if we have any feminine napkins for you to wear home, otherwise you'll probably ruin those pants. It looks to me that your panties are already ruined so I'll put those in the bin for you." He took a towel for himself and cleaned his cock off then used the towel to pick up my panties and dropped the whole handful into the bin. "I'll be right back." I doubted that my panties would stay in that bin after I left, but I figured if he wanted a pair of my dirty panties that were filled with another man's cum then why not let him have them.

He returned shortly with a feminine napkin and I put my pants on, positioning the napkin to absorb any leaking. I stepped up to him, wrapped my arms around him and gave him a deeply passionate kiss. He moaned into my mouth.

"Should I schedule a follow up visit?" I asked.

"I think next Friday will be fine, same time."

I turned to leave. "Regina," he said, I paused in the doorway and turned back, "you drive me crazy."

I chuckled, "Good." I turned and walked down the hallway, I could feel his eyes on my ass.

In my car I texted Michael, 'Doctor caught me with my panties down gave me another dose of cum now I leak from two places'. I hoped that thoughts of cum dripping out of my asshole would fill his thoughts for days and he'd want to claim it as his own soon. I knew that having his fat cock in my ass would please us both.

I was nearly home when my phone signaled his reply, 'You know I love your ass, is Sunday good for you'. He couldn't wait more than a couple of days to use his cock on me again,

I liked the way this was going. 'Sunday at 1, I'll be ready' I replied.

Sunday came and so did I, my fingers kept wandering down between my legs, even before I got out of bed, and thoughts of taking Michael's big cock in my ass filled my mind. I put on my robe and went to the kitchen to make myself a cup of coffee. While it brewed I grabbed a yogurt from the refrigerator. Coffee, yogurt and spoon in hand I went out onto my balcony and sat at the table, it was a beautiful morning. I ate the yogurt and once again those thoughts filled my head. As I sat there sipping my coffee I found my hand wandering down between my legs. My balcony was enclosed by solid walls on each end, separating mine from the neighbors on each side. No one could see me unless they were at the apartment building across the street looking out their windows, and it appeared no one was watching, though if they did look they would only see me in profile. I slumped in my chair, spread my legs, and began giving myself a good fingering. I opened my robe and laid my head back, the morning air felt fantastic between my legs and on my tits. Soon I was quivering with a good cum. I sat there catching my breath and I continued to leisurely stroke my pussy. I raised my head and reached out to my coffee cup.

That's when I saw him. He was standing in the window of an apartment across the street one floor up from mine. He was naked and looking directly at me with his hard cock in his hand. He looked to be about 20, which would make sense as there were a lot of college students who lived there. His blonde hair was short and curly and his body appeared to be muscular, as if he worked out. His right hand encircled his young uncut cock.