The 60-year-old (virgin?? )
My wife and I are in our early 60’s married almost 45 years we have 4 kids grown and out of the house and her younger sister lives with us she just turned 60 she has never married but had a boyfriend when she was in her late 20s he was the one that took her cherry.
Over the years of working my wife has developed some recurring issues stemming from injuries we have enjoyed a very healthy sex life for all these years, in the last few months she has been having muscular pain, in her back and legs so sexual activity has ground to a near halt at first i thought maybe she was just tired of sex and was making things up but after hearing her talking to a friend our age, I realized she was still very much interested but the pain was getting hard to ignore.
I was not supposed to be hearing this conversation, but I did, her friend was married 4 times and had not been married for 20 years, she recently had breast cancer but beat it, sadly she lost both breasts he had some implants to get the shape back but she had not been with many men over the years since the cancer.
She suggested that to help keep me happy I should find a stand in for my wife. A few days later my wife came to me and said she had talked to a friend and then to her sister now my sister-in-law at 60 had not been fucked or touched since she was 30. My wife suggested to her sister she should help take care of me her sister agreed but told my wife she had not fucked since she was 30, she said when she showers, she can hardly slide a finger in her unused pussy. My wife asked if I was willing to allow her to help out.
During all these years I had always wondered about her and when I found out about such a prolonged abstinence, I had to admit I was shocked to say the least but I said if she was willing I was willing I mean a hall pass and I was not feeling like so celibate.
My sister-in-law Tish although older now she still filled out a pair of shorts like a teenager her figure was still incredible! So that evening after dinner my wife said she was going to her friend's house and it would give Tish and I a chance to explore see if it would work out. Tish was clearing the dinner and taking care of leftovers while I filled the dishwasher.
When I finished i heard the T. V. on and thought Tish was in the front room she was not there so I shut off the T. V. and heard Tish call from her room, Todd?? Can you come here? I walked into Tish’s room she had a tall 4 postered bed with curtains and silky vails overing it she was on the bed she had a pair of yellow panties on and no bra,
This was the first time in my memory I had seen Tish without clothes. I let out a breath she was the sexiest 60-year-old I had seen she still had her natural red hair on her head her nipples still pink freckles crossed her chest her belly was a bit plump but still soft and smooth.
Her legs were still well muscled tan from riding her bike daily and walking on the local beach. She had a mischievous grin on her face she had a lock of red hair she was twirling in her fingers, and the other hand was caressing her leg and hip area. I must have started drooling as soon as I saw her and my nearly celibate cock sprang straight up in my shorts.
She said Emmy my wife had asked her to help with my predicament and looked at my eyes with her green bright eyes and asked will this do? She gestured over her body her and stopping just as her panties I was stunned.
I could only nod as the sudden rush of blood to my cock numbed my brains. Tish giggled like a schoolgirl at my shocked surprise. She seemed comfortable like this was an everyday happening. She took control and said it is fair to tell you I have not been fucked in years, and I am understandably scared, shy, and mostly tight as hell!
I again nodded my understanding. She held up a manicured finger and wagged it at me to come over i got to the bed side and Tish said Todd you can't fuck my pussy with clothes on now, can you? I started to snap out of my surprised state and said oh my you are right I can’t. I took my shirt off and tossed it on the floor on the pile of Tish’s clothes. Her hand reached through the silky vails and traced up and down my chest running circles around my nipples and tickling the tips her fingers trailed down my belly stopping at the top of my shorts she looked up at my face smiling as I hooked the tops of my shorts with my thumbs I started to push them down my legs and without looking down Tish's hand and fingers followed to band of my shorts just as the band passed my cock it sprang out her hand resting on my cock her eyes never leaving mine her hand wrapped around my cock and she let out a small gasp and moan I let the shorts fall and puddle at my feet not once taking my eyes from Tish's eyes.
Todd! Oh, my this is very big Emmy didn’t say it was so big she said I’m not sure but then she finally looked down. I am not what I would consider huge, but it still is about 6 and a half inches, and it is still thick my wife said after a quick fling with a co-worker from another state a few years ago at a convention she told me I was thicker than that guy but he was longer than me.
I moved on the bed I could see excitement and a bit of fear in Tish’s eyes she had not released my cock as I laid back Tish’s mouth started rubbing over the head of my cock her tongue flicked around it she pushed her mouth over and soon I could feel the back of her throat, she gagged almost immediately she grinned and giggled I have don’t that in a long time she put it back into her mouth and slowly swallowed me to see how far she could get it she then started bobbing her head over and over spitting on my balls and rubbing them she was in a position beside me where I could reach out and rub her cunt through her panties her body shuddered a bit as I ran my fingers lightly over her clit she also let out a soft moan around my cock.
I slipped my finger inside the leg of her panties and felt her slit was wet, I could feel her pussy lips full and thick her clit sticking out of its hood hard as stone I rubbed her clit up and down tickling it I could feel her breath slowly getting raspy around my cock I could feel her inner thighs starting to quiver a bit I knew she was building suddenly she arched her back like a cat, and her teeth started biting at my cock as her whole body started contracting she took her mouth of my cock and screamed “HOLY SHIT!!! ” I’m CUMMING!! Her body started bucking her hips trying to push her cunt on my hand harder in the spasming of her hips my finger moved to her cunt hole and my finger started to slip in she suddenly stopped shuddering her eyes had gotten wide, with the tip of my finger just barely inside her hole she looked and me and silently mouth OH, FUCK !! And her body started heaving again.
Tish calmed down from those orgasms, and she laid her head on my chest panting her eyes spinning some sweat beaded up on her forehead and upper lip. When her breathing calmed down, she looked at me with her face still flushed Todd, I have almost forgotten what that felt like, it has been so long. I smiled so long? With a man? She shook her head no just having one it has been years, I kind of got out of the habit of masturbating a long time ago.
Tish, are we going to still fuck? She looked at me surprised, are you kidding here help me get these panties off i pulled her panties down and was thrilled to see a delicate red trimmed bush under her panties she smiled, I did that today for you... I WAS a huge untouched jungle, i had gardeners offering to clear it out for free!
I laughed through it all she still had a near death grip on my now throbbing and leaking cock she laid back on the bed and spread her legs i got up in-between them I could see her wet glistening pussy lips hiding her entrance I moved closer and she reached down to hold her pussy open for me and I saw it was tiny her pussy hardly larger than my finger tip, it stopped and slipped a finger into the opening she winced Unnngghhh. Slowly Todd it isn’t as open as I was hoping, i told her to wait a second and ran to my room for some lube to cover my cock with and her pussy.
I had a hold on my cock and aimed it right to her tight pussy hole and tried to push my cock inside, the head popped in but she was too tight and to tense she was moaning softly in pain as her hand shot to my belly and her legs clamped around my hips she pushed me off and i could see tears forming in her eyes, she told me those were from frustration. She told me to turn on my back, and she would sit on it she said it was how she lost her virginity but as she was spreading more lube on my cock, she said that guy just wasn’t this big he didn’t have a man cock like mine.
Tish mounted my hips and reached down and pushed the head of my cock between her pussy lips and started to push down the head popped back in but only another inch followed she held it there her face reddening from the effort and the apparent pain then she got off she got up from the bed and ran into the bathroom I could hear the gulps of sobs I tried to come in she had locked the door, I knocked she said through the door that I should just leave she was embarrassed and ashamed. I tried to reason with her but heard the shower come on so I got dressed
I walked the short block to Emmy’s friend's house the women were in the theater room in plush chairs sipping on what looked like their third bottle of wine, Emmy looked up and asked slightly slurred speech well did Tish enjoy your cock? I sat down next to Emmy she could tell in an instant she asked what happened i recounted every wet detail including the unsuccessful attempt to fuck I told her I left her in the shower crying told Emmy she wouldn’t even talk to me I got scared and came over here.
Emmy looked at Pam her friend and said I must go Pam nodded i found Emmys glass and took a big gulp from its Pam said I’m just keep Todd here looks like one glass of wine won’t do it Emmy left without another word.
Pam refilled my glass another time and got up to go get a couple more bottles I was just finishing my second glass running the event through my mind Pam broke my thoughts i guess that didn’t go so well i looked up at her face smiled, who do you think suggested a surrogate for you? She sat next to me and continued I suggested that she let me help you out, but Emmy thought Tish would want the first offer.
I said it was great till we tried to fuck but it wouldn’t go she ran off crying Pam ran her fingers through my hair that must have been rough i nodded Pam slowly stood up and faced me she unbuttoned her jeans and started sliding them down she left her pink panties in place she kicked off her jeans and smiled, Todd, you need this I can tell she started unbuttoning her shirt I’m going to leave my bra on, I hope you don’t mind but you can treat them like the real thing. She started sliding her pink panties down she had very sparce downy hair patchy her and there she blushed; it used to be full and thick but after treatments it has just started coming back in.
I looked around my cock throbbing looking at this 50-year-old hottie, Pam told me like Tish there has been no man inside her in years, but she used a dildo from time to time she sat down next to me again and slide her hand under my short she looked surprised and said damn Todd, that is bigger than Emmy told me. With that she reached up and kissed me then pulled my shirt off, she started kissing me down my chest.
Her hand slowly stroking my cock she was licking and nibbling my nipples I could feel my cock running with precum I stood and pulled my shorts down Pam let go I watch her put her fingers to her mouth covered with my juices Oh, it has been a while since I tasted that I looked at Pam and said I’m sorry but I need to get inside a pussy.
She smiled and spread her long legs come on, it is wet waiting and VERY ready she grabbed my cock and pulled me on top of her I felt her legs wrap around my back as my cock found her hot wet entrance I pushed slowly I could feel her pussy opening up she sniffed and said enough of this slow shit and she shifted her legs and pushed her pussy up to my cock it sunk in all the way Pam when I hit bottom Pam exploded in a shuddering orgasm I could feel her pussy squirting on my cock and balls she hissed in my ear.... come on Todd! Fuck my pussy fuck me hard she was tight wet, and it was burning hot inside her female furnace.
It felt like 2 minutes, but it was about 20 we moved from missionary to cowgirl to doggie her pussy squishing with each stroke her our breathing fast and shallow her moaning louder with each orgasm her pussy clamping on me at times almost pushing me out only to have it slam back in, Todd!! I’m going to cum!!! , don’t stop!! Don't cum yet it has been so long!!
After a few more minutes Pam reached down and grabbed my balls as my cock pounded her wetness, I knew my cum was going to flood her I told the room I was going to cum Pam flattened out on her stomach my cock didn’t miss a beat suddenly I exploded firing deeply painting her cervix with glob after glob
Pam’s pussy grabbing at my cock not wanting a drop to escape. I could feel her ass muscles along with her pussy muscle shaking her pussy had a hold on my cock as it deflated inside of her body I rolled off and landed on my back next to Pam our breaths still fast and hard Pam said finally next time you get behind me don’t forget my ass needs loving I promised I would not leave it empty.
As i laid there Pam softly stroking my cock the world suddenly came out of the fog I shot straight up Emmy was sitting one of the chairs facing us her skirt up around her hips her panties around her upper legs he one hand buried in her cunt the other holding a bottle of wine.
Pam sat up next to me her hand still lazily stroking my cock Oh hi Emmy, sorry I couldn’t help myself and you didn’t tell me that cock was thick as hell I am going to be walking funny for a day or two, Emmy smiled I could tell she had rubbed herself to a couple orgasms don’t worry about it Pam, I was coming back to ask you to fuck Todd, and I am glad I didn’t miss the show!
As we walked back home, I asked about Tish, Emmy said she was fine she was incredibly scared she had let us down. I calmed her down and tucked her in we when to bed Emmy was holding me close her hand cupping my balls till, we went to sleep.
The next morning i woke up it was Saturday I rolled over and snuggled with Emmy but was shocked to find Tish in her place she smiled and said Emmy had gone shopping with Pam Tish went on she was trying to apologies about the night before I assured her there was no reason to be worried she laid on her back and grabbed my hand and guided it to her flaming red bush I smiled and said going to try it again?? I was running my hand through her slit and where her canal should have been there was something hard it has a little knob, I looked at Tish, she said Emmy had found the dildo we had made years ago from a mold of my cock and it was buried inside of Tish's pussy Tish told me that her and Emmy had worked it inside her before Emmy left I think you are going to fit now Todd!
We pulled the dildo out of her pussy with a slurp, and she immediately sat on my cock it fit like a glove she took a deep breath hold on Todd, don’t move it’s big! Tish sat still for a minute I could feel her cum dripping out on my balls she started slowly moving up and down the friction was maddening my balls bubbling pushing a hot load to my cock she nodded and started moving faster she was nearly a natural she ground her pussy on my cock straining to get every inch she noticed the head of my cock pushing out her belly I was holding her hips trying to slow her down I wanted this to last as long as I could i suggested she get on her hands a knees she had not ever done it but was willing
I was behind her grinding my cock in as deep as I could her legs slipped out from under her, I started pounding her into the bed hard and fast. She looked back at me over her shoulder her red curly hair covering her face she was squeaking loud and hard she made a high short sound with every pump, I could see it in her face before she said it she yelled out I can hold it and she was overtaken with the largest orgasm of her life somewhere in the middle of it Tish passed out just to wake up realizing she was still exploding, wave after wave I couldn’t hold out any longer I fired spurt after spurt into her belly mixing with her own cum i was just finishing up the shudders stopping i looked up and Emmy and Pam were standing in the door watching Pam spoke first it cause Tish to jump in shock Todd next time you fuck me you better give me that Tish rolled over on her back cum mixing in with her red bush, Pam looked at her and licked her lips I’ve never seen a red bush before!