Jan!

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My daughter's friend.
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Momstheboss
Momstheboss
3,114 Followers

I generally show up for choir practice 20-25 minutes early to talk and chit-chat with whomever is so inclined. A good while back, Nikki, a newly married young girl in her early 20s sat down next to me and congratulated me on my 42nd anniversary of marriage. The congregation had sang to us and applauded the prior Sunday.

"Nikki, please tell me you are not that naïve to think that married to someone for 40+ years is all a bundle of roses?"

Her smile disappeared and I felt bad immediately. I laughed, slapping her lightly on her jean-ed knee, and told her I was just joking and that while there are always ups and downs, that, the years will pass too quickly and have more happy times, then sad. I added I would not change a thing, which was true. It almost brought a smile back to her face.

The young lady had caught me on a bad night as I was having a pity party. You see, I had lost Peggy right after our 42nd anniversary. Bless her heart, on Peggy's list of things to do, sex was at the very bottom. Not, that I am not at the top of all other family oriented items, I am! Well, after our kids, then grand-kids, then comes me. I'm third in every other way, accept sex. She had been the perfect partner, but not the perfect lover. We argued the first 15 years of marriage and then I just gave up and accepted my fate, masturbating a lot. I could not help but feel misled as, during the 14 months we courted, she did not refuse one time to spread her legs for me to eat her pussy, then, jerk me off in a sock.

Now I'm not perfect by a long shot, but Peggy's excuse was that I was a grumpy man - becoming a grumpy old man - and hence she did not feel like screwing. "Why don't you just say you have to make soup? Meaning, if you don't want to fuck, one excuse is just as good as another. "Or, why don't you stop sitting on that treasure of yours and give me some pussy every now and then, then, maybe I would not be so grumpy!" Is what I would have liked to have said, but that would have really pissed her off.

Some years ago I began to have a fantasy. Should my wife go before me, I was going to spend $1000, of her insurance money, to pay for some woman to spend a minimum of five hours in bed with me. Why, $1000? I watched movies, I suppose. I knew which hotels downtown I could find such a woman. I had talked to other men, even a pimp, who told me for that kind of money he could guarantee me just about any type of woman I wanted. Then, there were other considerations; age, body weight, height, glasses no glasses etc.. The one thing that was not a question was her hair color, having to be a natural redhead, with a thick cuff to match, was a must. My dear Peggy had been such a gal.

As I had all my life, I looked at and studied women. Big, little, short, fat or tall - I loved them - everyone. After a month of grieving, the $1000 plan surfaced. It seemed disrespectful as I figured not enough time had passed. My hormones were flowing and after a masturbation session I put it aside. The months went by and each time I took care of the plan the same way.

A week ago, one of my daughter's best friends, Jan, knocked on the door. She inquired as to where my daughter and family might be. She was up from South Carolina making a round of her friends.

"Come on in, Jan. You probably past her on your way up. David's uncle had a stroke and they left the middle of the day yesterday to go see him in Greenville. Can I get you something to drink... Coke or iced tea."

"A Coke would be great, Mr. Baker."

My daughter, Betty, had known Jan since elementary school... had been members of our church and in the same youth group until they graduated high school. Though I had not had close, only occasional, contact with Jan, I felt like she was nearly family. Like my daughter, both were nearing 40. Through the years, I had heard conversations between my wife and Betty about Jan. Ken, their youth director at the church back then was my best friend. Now, a pastor on his own church, we have lunch often, we, discussing Jan often.

Working in another state at the time, Ken had made a special trip back to do Jan's wedding. It was a sorrowful event, with Jan crying, confused and generally unhappy. Ken had a short talk with her at the time, telling she could walk away if you wanted to. She was not pregnant. But, she was already being mistreated by her husband to be. Unfortunately, as Ken had figured, the marriage had lasted less than a year, with Jan afterward hooking up with a female. In the ensuing years, Jan would bounce from male to female and was a continuous topic with me, my daughter and Ken and I. She was now and living with a much younger woman, Carol. Jan was the "butch".

"You always called Betty's mother, Peggy. Why don't you call me, Carl." I told her as we sat chatting at the kitchen table. "So, are you content and happy living in South Carolina with Carol? I hear you have a good job at the nuclear plant?"

Ken and I discussed Jan often and whether she was a true lesbian, as she confessed, or, had been hurt by too many men, not trusting any of them. We both agreed that Jan loved to talk about sex and presumably engage in it. I teased Ken, a preacher mind you, that if his moral fiber was not so strong, Jan would have seduced him long ago, given the opportunity.

"She does like to be graphic." He would laugh.

"It's a good job but I am supporting Carol and her lboy." Jan answered. "We want to take us, and him, to Alaska but it's hard to save. I have a pretty nice house and everything is so expensive."

"That's a nice car you are driving too."

"You like cars! Betty tells me all the time."

"Your Alaska trip? How much you figure that's going to cost and how much do you have saved up?"

"About $7000. I've managed to save $5000 but it's getting harder. Maybe another two years... three at the most, I figure."

As we chatted, I had been studying the girl - no longer young - woman. She was short, probably 4'8", dirty blonde hair with a pigtail that just touched her back, ample in body, but not overly so, heavy breasts and thick thighs, she wore shorts, her smooth, toned thighs catching my attention immediately upon opening the door. Her most prominent feature being her large ass. She was definitely ass heavy! She was pretty enough. Most importantly though was my premise that she was a sex addiction and more than likely willing to step into the shade if not the dark-side. Did I mention she had dirty-blonde hair?

"Long-term planning. That's the way to do it." I said, then added. "But there's a chance that I could possibly help you make that dream come true. I would love to see that boy... you said he's 11... see Alaska. He'd remember it forever."

"Yes, 11. How do you mean, Mr... Carl?" She asked, curiosity in her tone.

I proceeded to tell her my thoughts that I have related to you with few exceptions - not slandering my wife in any way. I told her I had the money to spare. I laid out what I desired in return.

"My past is jumbled, I admit. But Carl, I am not a prostitute." She answered, without tone of injury.

"I was not implying that you were. I was only proposing that we help each other." I replied, without trying to sound apologetic and took a calculated risk. "How about this, Jan? Regardless of your decision, you get the money."

"I'm a lesbian, Mr. Baker... Carl! We use dildos occasipoally, for Carol, but I hadn't been with a man in over 4 years. I don't know if I can... could...do justice."

"Hey, I've been a lesbian all my life." I joked. "I think you'll do just fine.

"$2000 would buy you a sexy, good-looking woman. Much better looking than me."

"My instinct tells me you are ideal. And, though we have never been close, we know each other. I don't really care for a stranger, in this instance."

"Would you want me to suck...to give you oral? You're not going to want to stick it in my butt?"

I could not help but chuckle, but replied, "I'm a simple man, my dear. Peggy never gave me oral, but a couple of times in college one gal did. But I must insist on getting my head between YOUR legs."

"When do you want this to happen?" She inquired, telling me she had accepted.

"It's almost 4 o'clock. We could go for it right now, or, you could come back later on this evening. Your call."

"Well, there's no time like the present. Are we going to use your bed...the same you and Peggy used.?"

"That would be best, if you don't mind?" I replied. "I'd like us to take a shower together first ... to get to know each other."

"I find it erotic us doing it in the same bed. I'm headed home from here. I could use a good hot shower. Shall we?"

"Let me close some blinds and close a curtain or two. You can go ahead and get in the shower. I'll be there in a minute."

I studied her walking from the kitchen. I felt comfortable with my decision and extremely happy she had not taken offense. Me offering her the money either way may have convinced her. But maybe I was right in assuming that any sexual adventure would motivate her.

I entered the relatively small bathroom with a walk-in shower and undressed, letting my clothes fall on top of hers. I pushed all to the wall with my foot. I pulled the curtain back a bit and peeked in. She was facing away from me and I studied her from top to bottom, smiling as my attention focused on her ample ass. It appeared firm. I stepped in and lathered up a washcloth as she rinsed the shampoo from her hair. I began to scrub her back and shoulders. She glanced behind her with a smile on her face.

Jan showed no sign of embarrassment or self-consciousness as she turned to face me. I immediately noted her nipples were hard and erect. She showed a bit of belly, whick I deemed sexy. I was ecstatic when I saw her thick, forested mound.

"My, my, Carl. That's impressive. How old are you?" She inquired with humor in her tone.

I explained to her the truth. I had very little trouble getting an erection at my 64 years, but sometimes, usually, it did not last. I told her I suspected it was because my wife lost interest after having in orgasm, which generally I gave her first, giving her oral after screwing a bit. I hate to admit it, but my body visibly trembled when she reached to take hold of it, saying, "this could be interesting. I used to enjoy a good cock."

We scrubbed each other extensively, hugging, lightly kissing her lips and breasts, occasionally suckling, and grab-assing for perhaps 20 minutes under the steaming water. I toweled her off, then, she toweled me off. I initiated more kisses that turned passionate. She initiated the passionate french kissing. I followed her back through the kitchen as she sashayed to the back room, the far right serving as the bedroom. With curtains drawn, there was plenty illumination. My left hand was on her left buttock as she kneed herself onto the bed. I stopped her in place and lavished many kisses on her smooth ass cheeks before letting her roll to her back. The bedding was still in place. She lifted her still damp hair to free it, spraying it across the pillows.

"You mind if I take a few moments and study it?"

"Of course not!" She answered with a hint of glee in her tone.

I maneuvered to her right side as she spread her left leg, leaving it straight, but bending her right knee, her foot tilted on the bed from leaning her right knee wide, giving me an unobstructed view. My head close to her instep, I propped myself on my left elbow and reached to palm her mound, running my fingers through the dense pubic hair, up to her belly, rubbing it softly, fingering her belly-button. Returning to her mound, I pulled my forefinger down as if inscribing a line through her moderately lipped labia. Repeating, teasing the crack, then lingered in the area I figured her hole to be. I found it intriguing that she pushed against my finger, trying to insert it into her, a serious look now on her face. I flipped my hand over and let her probe herself until it slipped into her up to the first joint, then the second, all the while blowing air through her lips, while staring between her legs. She began to flex her crotch, riding my finger, mesmerizing me, until my finger was totally inside her. I concentrated on keeping my hand still, letting her guide the action.

She was now smiling at me. "If I make myself come, don't worry I'm good for more than just one."

"Do you want to come like this or would you be happier with my tongue on your clit?" I quizzed.

"I desire that too, my dear." She answered. "You are my first older guy and I am content to do anything you want to do for me or to me."

I decided to let her continue riding my finger at her own pace to see where it would lead. She seemed to drift off into her own world and was soon moaning continuously, her eyes loosely shut, her ass lifting and thrusting onto my finger. I studied her tits as they jiggled like Jell-O, marveling at her hard, firm nipples. I toyed with my cock and was happy to feel it firm. I studied her belly, flat and smooth because she was lying on her back. I was anticipating seeing her soul expose itself in those brief moments when the orgasm took hold. I was not disappointed when her body stilled momentarily before quaking, her animal-like moan involuntary and loud.

As it faded, Jan opened her eyes, lifting her eyebrows, then, smiling, expressing what appeared to be embarrassment. I maneuvered quickly between her legs and put my face to her pussy, I began to explore every nook and cranny of her wet, well lubricated pussy, my tongue soon centering on her clit. I spent a few long moments there until I her renewed moans. I pondered - should I - are not? I decided to go for it, shoving my hands under her ass and lifting, then, sticking my tongue into her treasure hole. "You are fucking amazing!" She praised, as she humped my face, thrusting firmly to get my tongue as deep as possible into her.

My mood was to ravish her pussy. For long minutes, I alternated my attention to tongue fucking her and concentrating on her clit. I was conscious of her lifted head watching. Then, when returning to her clit, in short order, her breath caught as another orgasm flowed smoothly through her body, she breathing a long sigh of contentment as it evaporated, her head dropping back to the pillow.

As I maneuvered up, she, knowing my intent, pulled her knees aft and instinctively reached for my cock and placed it to her. My cock entered her well lubricated pussy with ease. Her pleasurable sigh told me everything I needed to know as I maneuvered to grab her ass with both hands, locking her in tight, making an effort to keep my weight off of her. I had no confidence in my erection and wasted no time. I began to fuck her with a quick paced rhythm, with determination to ejaculate, marking her pussy as mine, if only for a brief time. I pondered what might think of me fucking and ejaculating into her partner.

If I chose to believe, after two orgasms, that her actions were authentic; her moans, her knees ratcheting against my sides, her tight embrace, then, she received kudos for keeping the lust alive, hence, keeping my cock firm. I was enjoying our fuck like I had not done with my late spouse in years. I concentrated on her moans and groans. She sounded authentic and seemed lost in the moment like no true lesbian could be. When she started to taunt me with, "come in me", "fill my pussy", "fill my belly" "I love fucking you", repeating such phrases repetitively, I knew she was more bisexual that anything.

"AAHhhhhhhhhhhhhhh! fuckkkkkkkk!" I exclaimed, as my cock jerked numerous times.

I shape-shifted like a toy transformer, releasing her ass to cradle her, as I continued to fuck her more slowly, kissing her neck lightly.

"You've got some good pussy, girl!" I praised.

"Ummmm. And you've got a good cock. I knew you didn't have anything to worry about. Opp! There it goes. How long does it take to recoup?"

"I don't know. It might not. Why don't we take a quick shower and go get some lunch and see what happens when we get back?"

It would have been fun to take a back-country ride to lunch with Jan, but I was really hoping to get my cock wet a little bit more before we parted company. We settled for a nearby, but nice, eatery.

Returning home, Jan excused herself to the bathroom. I continued to the bedroom and switched on the computer, midway into the room. In a few short minutes, I had one of my favorite XXX-rated videos on the computer screen. The couple on the screen were fucking missionary when Jan appeared behind me, bending over to wrap her arms around me, putting her head next in mine.

"Now that's what I'm talking about!" She said lowly. "I love watching fuck vedios. Wow! Look at that cock pumping into her pussy!" The view now showed their genitals.

I glanced behind me and was surprised to see Jan standing there, wearing only her bra and white skimpy underwear barely able to cover her buttocks. I felt like the girl knew me well and knew what turned me on. Surprisingly, she continued doing exactly what I would have wished. She rolled my chair back a bit, coming around to my left and then bent over, supporting her torso on her elbows on the table. Her ass was positioned prominently and within easy viewing and touching. I reached to wedge my left hand between her thighs, palming the inside of the right thigh.

"Look! He's coming. Did you see that?" She chirped.

"No." I admitted, reaching for the mouse to back the video up.

"Watch!" She stammered. "Look at that! See his cock jerk. He's coming inside of her. Back it up again. I hope he's not wearing a condom!"

We watched the segment again and continued watching as he withdrew his cock, a spider string of cum stretching, then, snapping apart. He wore no condom, bring to mind we had not talked about "safe sex", though I knew there was no chance of pregancy on my part.

"Don't you love it!" She chirped.

Jan stood straight and stepped to her right to be directly in front of me. She reached to slide each thumb under the elastic waist of her panties, pushing them down over her ample hips, stepping out of them after they dropped to the floor.

"Wouldn't you much rather have a pussy right here in front of you that you can see and touch rather than that on the computer screen?" She said, bending over once more, using the computer table for support with her hands.

"You know me better than I know myself. This is a most delightful view. You are not shy at all are you, Jan?"

"I have agreed to please you and that is exactly what I intend to do. Anything you want to do. But, no, I have never been shy."

What I wanted to do right then was get a better view of her fur-lined pussy. I gently shoved the chair back a bit. I placed my hands against the inside of her thighs to indicate I wanted her to widened her stance. She did, and I gazed upon her pussy a short minute. Then, I palmed her pussy with my right hand, scrubbing it lightly, causing her to moan.

"Well, one of us has a quick turnaround time. You seem ready to go?" I praised.

"I am, sugar. And I hope to hell you are too."

I reached to unzip my cotton shorts, groping to release my cock, which I found firm... well, firm enough. I rolled the chair forward, careful between her feet, and squirmed in the chair, placing my midsection to playfully put the head of my cock against her pussy. I drew the head of my cock back and forth between her pussy lips.

"You are bad, bad, bad!" She chuckled. "It's amazing the things that you can do that you never thought of before. Are you having fun?"

"I am. Yes."

My answer was to continue to tease her pussy with the head of my cock, it becoming firmer with the play. She was soon moaning contently, twitching her ass in a playful manner. She then began bending her knees slightly, causing me to seek her hole. The head of my cock popped into her. She lifted. We played some more until she finally poked herself again. She bobbed until she was poking herself repeatedly with the domed head without much effort. Then, knowingly, she flexed her legs more, taking the domed head of my cock inside her. Playtime ceased when she began to ride my cock much like she had rode my finger, now, half my shaft inside her, moaning lustfully. I remained stationary letting her - watching her- fuck herself.

Momstheboss
Momstheboss
3,114 Followers
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