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Author’s Note: Thanks again to Eclecticwoman818 for her sharp eye for errors and helpful suggestions. As always, please vote for all the stories you read. It validates the time we all put in creating our stories and helps us to figure out what was good and what was bad. Comments are also welcomed, but if you find fault with something I’ve written, please state your point in a civilized manner. On the other hand, if you’ve really enjoyed the story, please feel free to gush about my talents to excess.
Finally after six months I knew that I had to find somewhere to donate my wife’s clothes. I thought about giving them to the Salvation Army, but my daughter suggested that her work clothes might be put to better use if they were donated to the local women’s shelter to provide professional looking clothing for women to wear to job interviews. By the time all was said and done, we ended up with six bags of clothes for the Salvation Army and four bags for the women’s shelter. My daughter said she would call her friend Jenny, who volunteered there, to make arrangements so I could drop the clothes off, The shelter was a bit leery about men just showing up unannounced since most of their clients were escaping from abusive situations. I remembered Jenny from when my kids were in school. She was a fairly tall brunette with a bubbly personality and really large breasts. I know, I know, I should’ve remembered her for more than that, but being a male, that was what was burned in my memory. I saw her a couple of times in the twenty years since her high school graduation, but her unrequited lust for my son caused her to drift apart from my family.
My daughter called to tell me that I could drop off the clothes on Saturday morning and that Jenny would meet me there. I loaded up the car and arrived at the arranged time. When Jenny opened the door, she threw her arms around me and squashed those soft pillows against my chest.
“Poppa Prescott” she exclaimed.
Most of my children’s friends had referred to my wife and I as Poppa and Momma Prescott since we would often act as chaperons when the kids went somewhere that other parents wouldn’t allow their children to go unaccompanied.
“I was so sorry to hear about Momma Prescott, you guys were always so much cooler than the other parents. I don’t usually read the local paper, so I didn’t know about the memorial service until after it happened.”
“Thank you, Jenny. I’m sorry about you not hearing about it until later, but those arrangements I left up to the kids since I wasn’t really too stable at that time.”
“I understand” she replied. “So how are you doing now?
“I’m doing pretty well, the good days far outnumber the bad. Between work, the dog and learning to do the household chores I never had to do before, I manage to keep busy. Nights get a bit lonely, but I’ve started volunteering, so that helps.”
“Where are you volunteering?”
“At the Bijou. I work the front door scanning tickets usually, but occasionally doing other things as well. It gets me out of the house and gives me a chance to interact with other people. Then when I’m done, I usually stop at either the Main Street Grill or The Pub for a beer before heading home. Who knows, maybe one of these nights I’ll even get lucky.” I answered with a chuckle.
Jenny laughed “I’m surprised there’s not a line of women around the block already. Hearing that there’s a single man on his own is like blood in the water to a shark.”
“Well, I kept my wedding ring on until recently to act as shark repellent. I needed time to process everything. And what about you? Not married or at least living in sin with some guy?” I queried with a grin.
“No, I’m just working selling insurance. It pays the bills and since I inherited my mother’s house when she passed, I’m able to live quite well on what I earn. I did almost got married a couple of times, but I thought better of it once and the other time he got cold feet, so I guess I’m doomed to be a cougar spinster. I understand what you’re saying about the nighttime loneliness, though.”
“Maybe you’re looking for love in all the wrong places then. Getting them young and raising them your way is a lot of work.”
We chatted about this and that for a couple of more minutes before Jenny helped me carry the bags inside and I helped her sort through the clothes.
“I can’t thank you enough for this donation. Most of these women don’t have suitable clothes to look qualified for any job other than McDonald’s or Wal-Mart. This will go a long way to helping some of them move on with their lives and provide a better life for themselves and their children.” said Jenny as we finished sorting the clothes.
She took me around and introduced me to the shelter’s director who again thanked me profusely for the donation before I said my goodbyes and got ready to leave.
“What time do you usually head to the bar for your one beer before heading home? Who knows maybe I’ll meet you for a drink and we can talk about my misspent güvenilir canlı bahis siteleri youth and all the things your children never told you about.” Jenny said with a grin.
“It’s usually about 9:30 or 10:00 depending on how crowded it is and how many stragglers show up late. If the music is good I sometimes stay and listen to the band a while, but there’s nothing coming up that appeals to my musical sense.”
“Okay, well, thanks again.” said Jenny as I got in my car and left.
During the ride home I thought about what a shame it was that it seems she was only looking for the young guys. She had an impressive chest with a cleavage you could spend hours in and a nicely rounded ass. It was different thinking of her like that after having spent so many years as a ‘good dad’ and not lusting after my daughters friends.
After getting home, I mowed the lawn, ran a load of laundry and fixed dinner before heading out for the evening. There are usually two people scanning tickets at the door, and tonight Annie, the volunteer coordinator was there with me. Annie was a short woman, probably five foot one or two, with curly salt and pepper hair and a nice body for her age which I guessed to be fifty five to sixty. She kind of reminded me of a hippie earth-mother type who had aged quite gracefully. One of the other volunteers had told me she had a longtime boyfriend so I never really considered her as dating material or someone who might be fun to spend an evening in bed with. Tonight though she seemed friendlier than usual but I didn’t give it much thought.
The show started at eight and the main act took the stage at nine, and by nine fifteen it was pretty obvious that the last of the crowd had arrived. Annie asked if I would go up and check the balcony to make sure that only members were up there. Balcony seating was a perk of membership with more comfortable seats, a bathroom of it’s own and, on busy nights, a waitress to get drinks. Tonight was not a busy night. The balcony was completely deserted so I decided to linger for a couple of minutes before heading back downstairs. As I watched some proto-punk band jump up and down and attack their guitars with no more musical talent than it takes to slam out power chords, I felt something brush my arm and turned to see Annie standing next to me, much closer than I would have expected. She smiled and asked me what I thought of the band.
“Well, a lot of people bought tickets, so they must have some appeal, but certainly not to me. I like musicians what actually have some talent.”
She nodded, and we watched for a couple of minutes before she leaned closer and said something that I couldn’t hear. I bent down in hopes that I could hear her a little more clearly when I felt her breast press against my arm.
“Let’s go to the projection booth, the sound isn’t so loud and you can still see the band.” she said. I nodded and followed her a few steps down the hall and into what had been the projection booth when the place still showed movies.
“They sound much better when you can’t hear them as much” I said after we had entered.
“Yeah, they do.” Annie replied. “How do you like volunteering? Is it as glamorous as you imagined?” she asked with a grin.
“It gets me out of the house and fills in some of my evenings. Those are the loneliest times since my wife died.” I answered. “Where’s Ken this evening?”
I had met her boyfriend once and he seemed like a nice enough guy, but it seemed the theater was more her project than a team effort.
“He’s off fucking his sister” she replied nonchalantly. “Well, his half sister actually, but since her husband died, he goes up to see her every month or two and satisfies her needs. I know it’s incest, but they’re both consenting adults and were well past the age of consent before they started screwing each other. We have a fairly open relationship, but he takes more advantage of it than I do.”
I stood there with my mouth open for a couple of minutes while I tried to think of a proper response to that admission.
“Well, as long as they’re OK with it and you and he are OK with it, who am I to judge.”
“And how about you, how long has it been since you’ve been with a woman?” she asked.
“It’s been a couple of years since I was with anyone other than Thumbelina and her four sisters. After my wife got sick, sex was the first casualty, and since she passed, I’ve struggled to recall how I used to meet women when I was single.”
Annie smiled and reached for my belt buckle.
“Let’s show Thumbelina that she’s not the only game in town.”
With that she knelt in front of me and unfastened my belt, unbuttoned my jeans and slid the zipper down. After pushing my jeans and boxers down, she pushed me back into a chair before starting to slowly stroke my cock. As I sat there bewildered by the whole situation, I started to get aroused.
“Oh good” she said smiling up at me “I was worried that he might be dead.”
When I was fully erect, she güvenilir illegal bahis siteleri leaned forward and placed a kiss on my head and teased the pee hole with the tip of her tongue. She was rewarded as my arousal sent a drop or two of pre-cum to tease her taste buds. She surrounded my head with her lips and started sucking with hollowed cheeks as she swirled her tongue around and over my swollen head causing me to groan my approval. Annie slowly lowered her mouth to engulf me completely.
“Oh, God that feels good. It’s been so long…it’s been soooo long.” I muttered as she slowly coated my cock with her saliva while massaging my balls.
“I don’t know how long I’m going to last, but I’ll try and give you a warning in case you don’t want me to cum in your mouth.”
She responded by sucking harder and faster. My fingers entwined in her curls as I felt that long forgotten feeling of impending release.
“I’m going to cum” I groaned before she teased the sensitive spot just below the glans and sent me into rapture.
Gripping her hair, my hips bucked and forced my cock deeper into her mouth as surge after surge of cum coated her tongue and filled her mouth. I stiffened as the last drops of cum oozed from my tip and onto her tongue. She slowly slid her lips up my shaft before letting me slip completely out. Annie looked up at me with a smile before opening her mouth to show me the fruits of her labor and then swallowing it.
“Feel better?” she asked as she stood up.
“Yes” I replied feebly.
“Good, so do I” she replied before leaning down and kissing me for the first time.
“I have to get going and check on the other volunteers before I go. I’ll see you soon.”
With that, she left and headed back downstairs. I sat there for a minute or two before realizing that it might not be such a good idea to be caught up there by myself with my pants around my ankles. I got up, pulled up my pants, and took advantage of the upstairs bathroom to relieve my bladder and splash some water on my face before heading downstairs to find my coat.
After leaving the theater, I headed up the street to The Pub to grab a beer. I found an open seat at the bar and ordered a Smithwicks, my mind still whirling from my encounter with Annie. As the acoustic duo launched into a passable version of Van Morrison’s Cleaning Windows, I felt a pair of hands on my shoulders and a pair of breasts pressed against my back, a voice whispered in my ear
“There you are, Poppa. I had about given up on you at this place and was going to look for you at the Main Street Grill.”
I turned to see Jenny standing there grinning.
“Hey, it’s my favorite cougar spinster. Long time no see.” I laughed.
“Well, it was so good to see you again this morning, I figured ‘what the hell’ and came out to see if we could catch up some more this evening. I’ve got a table over on the side, why don’t you come join me so we can talk without yelling.”
I picked up my beer and followed Jenny over to her table. We sat at ninety degrees to each other at the round table so we both could see the musicians and also so we could hear each other when it got louder. Jenny was wearing a pastel striped blouse that buttoned up the front, snug fitting jeans which hugged her curves quite nicely and a pair of high heels. We reminisced about the times she and my kids had, the party they threw at our house when my wife and I were away for the weekend and the stories about she and my daughter and their various boyfriends. After another drink, she confided that she had had such a crush on me when she was in high school and for a couple of years after. I smiled and told her that that was very flattering and that I never had a clue about it.
“I know. I was careful not to flirt around you because I knew that you belonged with Momma Prescott. But that didn’t stop ‘you’ from giving a sixteen year old girl pleasure when I was alone in my room.” she said with a slight blush.
“Since we’re making guilty admissions, I will say I do remember how well you were ‘developing’ when you ran around in your tight shorts and cut off t-shirts. It was nothing I would ever have pursued, but I did have a couple of dirty old man thoughts.” I said laughing.
We chatted and laughed about more of the crazy stuff she and my kids had done growing up, listened to the music for a bit and had another drink before I excused myself to use the men’s room. The entire time I was gone, my mind kept trying to make some sense of the entire day. Seeing Jenny this morning and her being very friendly, the blowjob from Annie at the theater, Jenny coming out tonight for the express purpose of finding me, the hints that she was readily available if I was ready. I cursed myself for not buying a lottery ticket for this evening, I probably would have been able to retire in the style I’d like to become accustomed to.
“So what are you going to do now?” Jenny asked when I returned to the table.
“I probably should head home” I güvenilir bahis şirketleri replied. “If I stay here and have another drink, I’ll become a candidate for a DUI that I neither need nor can afford. Besides, if I want another drink, I have a bottle of good bourbon at home. And if I get drunk, I can at least sleep late in the morning.”
“Ohhhh…What kind of good bourbon?” Jenny asked, smiling.
“I buy myself a bottle of Blainton’s Single Barrel every year at Christmas. It’s the only real vice I have left. I’m too old and slow to chase after women anymore and the one’s I could catch would either be even older and slower than me or dead, and neither of those options appeal to me.”
Jenny laughed. “You’re still quite a desirable man. You’ve got the distinguished gray hair and beard, you can hold a conversation about things other than the latest video game and you aren’t forever checking your phone to see what the latest twitter or instagram feed is saying.”
“Are you OK to drive?” I asked as I put on my coat.
“I think so.” she said just as she started to stand and almost lost her balance.
I reached out and steadied her to keep her from falling.
“I’m not so sure you’re in any condition to drive. Should I call a cab for you , or if you want, you can stay in my guest room and I’ll drive you down to get your car in the morning.”
After weighing her options, Jenny said that it would take forever to get a cab tonight, and they wouldn’t be happy about having to take her to her house since she was so far out in the country and away from the main roads. And then the time and expense of having to get a cab back in the morning would be another bother.
“You sure you don’t mind if I stay over?” she asked.
“I’ll have to call my other four girlfriends and let them know we will have company.” I teased.
After assuring her that she was more than welcome and also that I was certainly sober enough to drive, we made our way out toward the car. Jenny held my arm and pressed close to me as we walked the block to my car. As I reached around her to open the door, Jenny slipped her arm around my neck and pulled me to her and kissed me hard. Her lips parted and the tip of her tongue traced along my lips. I accepted her invitation and parted my lips to allow her tongue to dance with mine. My rational mind kept saying ‘she’s young enough to be your daughter’ while my libido kept saying ‘ way to go, you old coot’, As we ended the kiss, my rational mind regained control.
“Jenny, we can’t, you’re young enough to be my daughter.”
She looked at me very seriously “May I remind you that your daughter is almost forty years old and has made you a grandfather three times. That makes me old enough that our spending the night together is no longer creepy. After 24 years, I get to say thank you to the man who gave me my first orgasm, even though he didn’t know it at the time.”
After that, she grinned “You get to have your cake and, hopefully, eat it too. And not have to worry about going to prison for it.”
My libido flipped Mr. Rational Mind the bird as I leaned to Jenny and kissed her again. We broke the kiss when we heard people coming down the street.
“Let’s go before they think we’re a couple of teenagers making out on the sidewalk.”
During the short drive to my house, Jenny’s hand rested on my thigh, her fingers moving in small circles, almost like she was stroking her own clit vicariously on my thigh. After we pulled into the driveway and I shut off the car, we leaned close and kissed hungrily. My hand found her left breast and discovered her nipple was erect and straining against the fabric of her bra and blouse. She moaned as I pinched and twisted it.
When we broke the kiss I said “Let’s go inside. I want to feel those magnificent tits around my cock as I slide up and down between them.”
Jenny grinned as she reached for the door handle. “That sounds really hot to me. I love when a guy fucks my tits” she said.
We went in through the back door and as soon as we were inside, Jenny turned to me and dropped to her knees. Stroking my cock through my jeans she looked up at me with a smile.
“I’ve wanted this for a long time. You provided me pleasure not only in high school, but on occasion over the years since as well.”
With that she unbuckled my belt, unbuttoned my jeans and pulled the zipper down. She slid my jeans down before kissing my shaft through my boxers. She then reached through the front of my boxers and drew out my cock.
After admiring it for a few seconds, she said “I fantasized about this forever. I always pictured it as longer, but I’m not disappointed now that I see it. And it’s much fatter than I imagined.”
She leaned forward and kissed the tip and lightly along the full length of my shaft
I reached down and lifted her back to her feet “Let’s go upstairs first. Then you can get me wet and nicely lubricated so my little fat cock will slide nicely between those big tits of yours.”
I reached down and pulled up my jeans and held them as we climbed the stairs.
“Your cock is not little, it’s just that I had unrealistic fantasy expectations. I’ve always wanted to find a man with a 10 inch cock and in my mind you were that man. But what I just saw did not disappoint me at all.”
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