Cyndi and I had dated for about 5 or 6 months when it seemed it was getting serious. I'd met her divorced mom many times and she was a nice lady. Now it was time to meet her mom's mom. Her grandmother, Sherry, lived on the other side of our large metro area. We went over one Saturday afternoon.
Sherry was at the door greeting us as we parked and got out of the car. She had a warm smile and was super friendly. She welcomed us, hugging Cyndi and I, and invited us in. We had a light lunch with the usual chitchat, but I could not shake the feeling that Sherry was familiar to me. I found myself lost in thought as to why. I'd never been in this neighborhood and in fact rarely ever got to this side of town.
We talked and enjoyed our visit and Cyndi and I prepared to leave. When Sherry stood up and turned in profile to hug Cyndi I really noticed there was quite a rack concealed beneath her heavy sweater. It was January after all. I've always had a thing for mature women and even at 20 years old I was a MILF chaser - Cyndi didn't know and I was going to keep it like that.
Later that evening I went home and retreated to my basement bedroom. I still lived at home as this was my junior year of college and it was too expensive to go away to school and my city had three good universities so I lived at home and went to school. I also worked part time to earn my spending money - mom paid for school, insurance on my car and living expenses.
I went to my computer and was looking forward to rubbing one out watching Internet porn. Naturally as a MILF chaser I gravitated toward that. I also loved retro porn. I liked it when sex was dirty - ya know, the 50's, 60's, and 70's? Before an Internet when every girl in town wasn't naked on my computer. I was rubbing my cock and cruising retro porn sites when I stumbled onto a site that specialized in retro pinups, glamor models and burlesque gals from those bygone days.
I freed the fattie and was rubbing him, not really concentrating on any specific image or thought, just cruising the pages on this site. Every page had 40 or so pics on it. When I saw one that interested me I clicked on it. Usually that led to another page with numerous photos or videos of the woman I clicked on from the main pages. I spied one that really caught my eye and clicked on it. She was a youngish brunette with alluring eyes and a nice body. The second page had more photos of the brunette, but in many of the photos she was having lesbian sex with a woman called Lee Wyatt. I stared at the pictures. Something was familiar. I know I'd seen Lee Wyatt on these pages before and I had actually lost a bucket full of cum looking at her before. Then it hit me - it was Sherry, Cyndi's grandmother! I was turned on and shocked at the same time.
What a body! This Lee Wyatt was hot beyond belief. No wonder I thought I saw something familiar in Cyndi's grandmother when I met her. I had jacked off looking at her naked on more than one occasion. I was so dumbstruck I quit rubbing the big boy for a minute and just stared at all the images taking in each nuance. Unlike much of the pinup "lesbian" porn where the girls were just together laying on a bed or something, these two were eating pussy, sucking tits and my favorite - tongue kissing. My cock was throbbing and I came in about 30 seconds. I cleaned up and returned to the images.
Sherry/Lee Wyatt looked about 25 or so in the pictures. She was built incredibly well and had one stunning face to boot. I started recalling the things Cyndi had told me about her f****y. Her grandmother was a single parent of two girls. Her husband left her when she gave birth to the second k**, Cyndi's aunt Elise. He was a reprobate and alcoholic bad boy type. Sherry/Lee Wyatt raised them on her own never remarrying. She held down an office job and raised her daughters.
There were about 20 photos of Sherry/Lee Wyatt and the other hottie doing the nasty. I found a link on the page with the name Lee Wyatt and clicked it and it took me to her own page on that site. In addition to the 20 or so lez make out photos I'd found there were a few dozen nude, pin up and glamor type shots, all in various stages of nudity. And Lee Wyatt was spreading a shaved cunt in most of the photos and in one she's pinching both her fat tits by the nipples. Fuck! I thought to myself. This is so hot. I made plans in my filthy little mind to see Sherry again, and damned soon.
About two weeks later Cyndi and I were at Sherry's again. She lived in an older but well kept small brick home in an old neighborhood of tree lined streets. I looked around and saw a few things that could use some maintenance and offered to come back with some tools and help Sherry do a few things around her home. Naturally Sherry and Cyndi thought I was just the sweetest young fella they'd ever met. I beamed with devious pride and told Sherry I would come over tomorrow at noon and plan an afternoon helping her out. She said she'd order a pizza for me. I made like that was the greatest thing ever. Cyndi was so thrilled with me we went back to my house and fucked until almost midnight before she went back to her own home at her folks house. Cyndi had to work that Sunday at the department store where she was employed, so with her blessing I went to "help" Sherry.
I got to Sherry's a bit early, chomping at the bit. She just thought I was the nicest young guy in the world - if only she'd known . . . Sherry greeted me dressed for work - old jeans that fit her matronly form quite well and a green t-shirt underneath of an old, over sized flannel shirt. I remarked about the shirt and she smiled and told me she loved old, over sized clothing to wear as a outer layer to keep her warm. It was one of her son-in-laws old flannels - Cyndi's dad's to be more precise.
We discussed what needed doing and set about doing it - patching and filling a couple old nail holes pictures were used to cover on her plaster walls, tightening down the banister to the basement steps, securing the carpet runner on her hardwood steps to the second floor and she had two light bulbs burned out in the attached garage. I used her 6 foot ladder to replace the bulbs. She told me she was scared of heights. Naturally I asked her why she had a ladder then, and she smiled and very sexily looked me in the eye and replied "In case some handsome and strong young man comes by to help an old divorcee!" she quipped. I took in her words and her very flirtatious way of saying it. Of course I wrote it off to friendliness. It was about 2:30 when Sherry said "Is pepperoni okay on a pizza?" "Sure," I replied and Sherry said she was going to get cleaned up. She gave me a $20.00 and said "pay the man" if the pizza arrived before she'd finished showering and changing.
I waited patiently - well as patiently as I could considering my brain was running rampant with all sorts of vile scenarios in my head. The knock on the door came just as Sherry returned from upstairs. She flew down the steps and grabbed the money from the table, gave it to the delivery guy and returned with the pizza. We sat in the living room eating it. I admired her full ass as she sashayed it into the kitchen to return with two soft drinks to accompany the pizza.
Sherry was wearing a sweater over some clean jeans. It was not nearly so big and fuzzy as the one she'd worn when I met her. Damn! I thought - her tits were pretty large and matched her ample ass very well. I found myself thinking a lot of Sherry and not pizza. I couldn't get the retro porn images of her naked and eating pussy out of my mind. Sherry saw me sort of lost in thought and said very sweetly "Are you okay Cody?" She placed her left hand on my knee when she said it and I felt electricity. I looked at her. Her smile was sweet, warm and inviting, and her left hand was still on my thigh. "Yeah, fine Sherry. Just thinking," I said. "What about," she playfully asked. "About all the work to get this place back in tip top shape?" Naw," I replied, growing brave, so I thought I would drop a hint. "I keep trying to figure out why you looked so familiar to me when I met you a couple weeks ago."
Sherry almost recoiled a bit and very, very slowly removed her delicate small hand from my leg. "Me? Familiar?" she asked. "Yeah, I just keep thinking you're familiar to me, but I can't place why." She sort of laughed it off, claiming she was just another nondescript old woman. I corrected her and got bold in so doing. "Sherry, there is nothing nondescript about you!" She smiled "Really?" "Absolutely" I replied. "You're a real hottie!" She flashed a grin that was totally reminiscent of some of her pin up shots I'd seen on the porn site.
"You sure know how to flatter an old, dried up woman," she coyly answered. She was fishing for compliments and I was glad to oblige. "Jeez Sherry, from looking at you, Cyndi and her mom it's pretty clear women in your f****y age very, very well." I went on "If Cyndi ages as well as her mom and grandmother she will still be a stunner in her mature years, " I said, and then feeling really bold now, I added, "I think mature women are much more alluring than are younger girls really." Sherry cocked her head and replied, very forthright and to the point "I almost feel like you're flirting with me Cody!" "Me, flirting with my girlfriend's grandma?" I smiled at her. She shot back a knowing grin, "Okay then." I figured it was now or never. I added "Am I a bad person for flirting with a gorgeous woman, even if she is my girlfriend's grandmother?"
Sherry looked at me for a second. Her eyes burned through me and I got nervous thinking I may be in it now. "Actually Cody, it's very flattering to have such a studly young man flirting with me." I took that for all it was worth and looked her in the eye.I surmised that it was now time to lay my cards on the table. "Sherry, I have figured out why you're so familiar to me." She looked at me and I was unsure what to do next. I wanted to blurt it out but fear was mounting in me. That is until she led me on with "You do, huh?" So, where do you think you know me from?" she asked in a very inviting manner.
"Well, I don't know how to say this but..., you are very familiar to a woman I've seen named Lee Wyatt." Her eyes narrowed a bit and I thought she was going to play it off. "So you know, do you?" I almost fainted! "I knew that was you Sherry, or should I call you Miss Wyatt?" She smiled and asked me very sincerely, "Have you mentioned this to Cyndi perhaps?" "No ma'am." She smiled knowingly and seemingly reassured. "where did you see my photos?" she asked very gently.
I told her where and she was inquisitive. "Show me," she said. She got up and said she was going to get her laptop and disappeared upstairs. She returned almost immediately. She turned it on and went on "I haven't seen these pictures. Where are they?" I took the laptop and went to the retro porn site. I told her I was a bit embarrassed doing this with her watching and she patted my back and said "Wow, me too! Go on Cody!' she encouraged. I clicked through a few pages and there opened the page dedicated to Lee Wyatt. I turned the laptop toward her ad said, "there you are, and damned hot if I might say," I added felling a bit more bold.
She looked at the photos. "Well, I guess it's time for an explanation," she offered. "No ma'am, you don't owe me anything," I replied. Her eyes danced at me with warmth and understanding. "Well, can I explain anyway? It might be cathartic for me." "Sure," I replied and sat back on the couch and turned to her.
She launched into what was going on in her life at that time. She could not make enough to take care of two small daughters and then someone told her about adult entertainment and she could make quick, easy money, and she was desperate. She started out nude modeling, then did some pin up and softcore poses - no sex, but the suggestive lesbianism of those days - two or more nude women touching each others asses or tits, but nothing more. She was then offered $500.00 to do a days hardcore lesbian work with the other woman in the photos so she did.
She went on to tell me she was a low level administrative supervisor for a large company and earned about $10K per year, back then, in the early 1960's. She found the adult work to be enticing for the money only and that in just under three years of modeling and dancing at strip joints in another town 40 miles away, she'd made almost $50K in cash. She used that to pay for her home, savings and a car. She then put a chunk of it in accounts for her girls college educations, which neither daughter used, instead both marrying at about 20 years old, so she had a nice little nest egg. She had just retired from that very same company she'd worked at for almost 35 years and she was doing quite well on her saving, retirement income, investment income and was waiting to collect social security beginning next year when she turned 62.
She went on to detail how she'd dated some when her k**s were little but too many of her suitors were aware of her shady past and she tired of being seen as an easy mark. By the time her k**s were in high school she'd decided she'd rather be single than deal with that. And then she lamented how her daughters were always trying to arrange dates for her, fearing their mom was growing to be a lonely old spinster. She threw her head back and laughed at that then pointed to the pictures - one of her bent over showing her ass for the camera and said "Does THAT look like a lonely woman Cody?"
She went on to say that she was very happy alone. Of course she wished for more sometimes, but she'd been her own boss for way too long to want someone complicating her life. Then she looked at me and asked, very sincerely mind you, "Cody, are you going to complicate my life, young man?" I was shocked at her question. I stuttered a bit and said the only thing that came to mind - "Do you mean am I going to blab my mouth about this to Cyndi or her mom? No way! I can keep my mouth shut about stuff." Sherry smiled and leaned back on the sofa sort of breathing a sigh of relief.
"So, you like these pictures huh?" she asked sort of leading me where she wanted to go. "Well," I began "I liked sex better when it was ...ya know... a little dirty and forbidden." I then quickly added "I also sort of have a thing for mature women, and I like looking at stuff with beautiful mature women doing stuff that was sort of forbidden back then..." I trailed off, unclear if I was saying too much or the right things. "I wasn't mature then Cody...I was about 23 or so when I was doing this stuff." "Oh, I'm sorry Sherry. I didn't mean to say you were mature then...I just kinda meant...." "she interrupted me with "you mean you liked dirty stuff then and how that plays out in your little mind now?" "Ahhhh....yeah, that sounds sorta right." I replied.
"So, do I still look good, I mean, in your humble opinion?" "Oh my God yes, Sherry. You are way hotter now then you were then and you were real sexy then too!" Sherry looked at me and sort of leaned toward me, placed her left hand on my knee again and said "You're quite charming Cody. I can see why, in addition to your good looks and mannerly demeanor, Cyndi likes you so much...she does ya know?" she added. "Yes ma'am," I am pretty crazy about her too." Sherry smiled. "Then I guess you and I will be seeing more of each other perhaps?" I smiled sheepishly and said "yep!"
I also detected a slight bit of the dichotomy Sherry was hinting at that I was dating her dear granddaughter and flirting with granny. I figured I was on my way to being given the "Well, I hope you keep my confidence chat..." but was surprised when instead she looked at me and blatantly asked, "Do you want me, Cody?" "Fuck yes!" I replied, almost out of my mind. Sherry smiled and said, "And this is and always will be our little secret?" "Yes ma'am, no matter what ever else happens, my lips are sealed. I would not rat you out to your f****y. Besides, that's just not cool and I would never consider blackmailing you or anything like that..."
She cut me off and fluttered her eyelashes at me, "Well that's good because I could only in my mind justify having sex with my granddaughter's hunky boyfriend if I was f***ed into it..." I got he message. "Ya know Sherry," I said as she rose and sashayed her plentiful ass and tits toward the kitchen... "I think what I have seen is going to be hard to keep to myself...unless of course someone sort of rewarded my silence..." I offered. Her eyes lit up as she looked over her shoulder at me. Her eyes were making me dizzy the way she was looking at me. Suddenly I felt like a piece of meat and she was a damned hungry dog.
"Be right back,: she said as she carried the half eaten pizza and sodas away. I sat about to shit myself with lust, fear and wonderment as to what next, but I didn't really have too much time to consider it. She emerged from the kitchen with two more fresh sodas in her hands. She walked by me really swaying her ass and tits for me. She had her evil green eyes locked on me as she did it and she headed for the stairs.
"Hmmmm...." she sort of thought out loud..."I wonder if there is anything up in my bedroom that needs your attention Cody?" She turned and started up the landing. She stopped as she got to the second step, stopped and whispered to me, "Lock the deadbolt Sweetie, and let's see what you can work on for me...I'm sure there are some things that only a strong and sexy young man can take care of." I was staring and she taunted me..."Are you coming?" "Not yet," I grinned. She looked at me quizzically and then realized I was playing with her words. "Well, maybe with the work I have in mind for you there will be plenty of that!"
I jumped up,. turned the dead bolt and ran for the stairs. She squealed like a little girl and ran away from me up the stairs. I chased her, followed her into her room, took the two cans of soda from her, sat them on her dresser and grabbed her around the waist. "Oh, young Mister Cody, why, what are you doing c***d?" She playfully asked. I turned her around. "I hope you're not going to strip me naked before you and do all those things you're young and I'm sure very strong libido would like to do to a helpless old woman." Her lips were almost on mine as she whispered that to me. I kissed her and she hungrily sucked my tongue into her mouth.
I didn't need to strip her...she did it for me and faster than I could drop my own pants. Once she was completely naked she pushed me away and cooed "Would you like to get a nice view of what it all looks like 35 years later?" she teased. I just nodded, my mouth hung agape. She proceeded to get on the bed on her knees and strike some of the poses from her photos. "Like what ya see Cody?" she purred. I nodded. "She looked at my cock and added, "Well, it seems you're telling the truth by the looks of that gorgeous thing down there."
Bold and determined now, I replied, "Would you like me to show you Sherry?" She nodded knowingly. "I sure hope that strong, fat cock doesn't fuck me to death, but then again, we all have to die sometime." I jumped on the bed and we rolled all over, kissing, fondling and all the rest,. We fucked until nearly dark. We both were exhausted and grinning from ear to ear. I didn't want to go and she didn't want me to but we agreed if this was to continue, we needed to be discreet.
We talked about the future of this tryst as we dressed. She came to me and held onto to me kissing me passionately as we fantasized of future situations. Then she sealed the deal in my mind. She hefted my still uncovered cock and balls and offered "I hope it doesn't make me jealous knowing that beautiful cock is fucking my granddaughter instead of me all the time." "There's plenty enough for both of you, " I said, feeling, pardon the pun, cocky!
Sherry smiled at me sort of like a little girl and said "It's okay Honey. There is surely plenty there for me too." Then she really shocked me when she addressed a thought that had already passed my filthy mind as I fucked her. "Gee, what if you married Cyndi? Wouldn't that be something?" She looked happily pleased at that thought. I stated scheming in my mind. Cyndi ate pussy because we'd fucked her friend Rachel a few times, and Cyndi loved it when she watched me fucking Rachel while she ate her pussy. I knew Sherry ate at the "Y" and naturally, being the filthy minded little bitch I am, I smiled at the potential.
"Yeah, that would be Heaven Sherry. Wow. Me Cyndi and Sherry the former stripper. Now that will make me hard as a rock again," I smiled at her. She rubbed my still not covered cock as I slipped on my t-shirt. I left my cock and balls uncovered to tantalize her even more, and the effect worked because by the time I could pull my shirt over my head she kissed my ear and breathlessly whispered "I'll bet in that nasty mind you see the three of us making love together, don't you?" I smiled and my jaw dropped open and hung in disbelief. "Would you like that Cody?"
I just stared at her. She fell to her knees and started sucking my cock again. As she did so, she said "Tell me what you'd like to see us do Cody." I did. She sucked me until I dumped a fourth cum load, this one on her face, lips, nose and a portion of it into her mouth.
She helped me slip on my britches and told me to scoot. "After all" she said, "there's plenty of things around here need keeping up with in the future. Can't fix them all in one day, right? I hope we'll talk soon. I gave her my cell number, she gave me hers and she e****ted me downstairs. I stopped at the door and turned to her. "Cody, I don't know where this goes from here, but I hope we can see each other again, and soon I hope." I assured her I wanted that as much as she did. And then she really drove me crazy.
"Now go home and turn on your computer and look at me naked some more. Next time....there will be a next time, right... next time, I can tell you about some of the interesting things my alternate activities led me to do. Bet that would fire you up even more." I kissed her as I smashed her up against the door. I pinned her and she was all hands and tongue. "Jesus Sherry, you're making me crazy for you again." She just patted my bulging cock and save "Well go home and relieve it. If you want you can call me and we can talk while you do it!" Her eyes betrayed the most sexual woman I have met in my young life thus far. I gave her a peck on the lips, ran out the door and hurried home. I checked to make sure her number was in my pocket - it was.
Jesus, this was going to be the most awesome time of my life I guessed. If only I'd have known it was merely the beginning of a sexual situation that would hold me ensconced for a decade. But that's a story for another time.