Hope That We Can Stay Friends

by Small Penis


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by MisterReason

 

The visit that Oliver Wells paid to the house of his soon-to-be ex-mother-in-law could have been very awkward, given the fact that the 27 year old accountant was going to be officially divorced from his wife of five years any day now, but because he had always gotten along famously with Jill’s mother Pamela the trip to retrieve some belongings turned out alright.

In fact, as Oliver had noted during dinner, it seemed that during much of his courtship and marriage to Jill he had gotten along better with her mother than he had with his wife Jill.

After the items he chose to keep had been packed into his car, when Pamela Cole insisted he stay for dinner Oliver eagerly accepted while noting that without Jill to go home to there was no rush to go back there.

The dinner came with a couple of glasses of wine, and when the petite middle-aged woman suggested that Oliver spend the night instead of driving all that way back, her son-in-law took her up on the offer.

“Just like old times,” Pamela Cole said as she straightened up the guest room where her daughter and Oliver had slept when they stayed over in better times, “And after you get ready for bed you can set your clothes outside the door and I’ll have them washed and dried for tomorrow, just like a fine hotel.”

“I can’t have you do that,” Oliver protested meekly, but he relented when his mother-in-law insisted.

“But first we have to finish the wine,” Pamela said, so they retreated to the kitchen to have some more wine and reminisce before they turned in.

Dutifully Oliver got undressed, checking to make sure his underwear were still fairly clean before setting them outside the door and scurrying under the covers of the bed.

Oliver looked at the shadows dancing on the ceiling from the moonlight filtering through the trees outside, and as he thought of Jill who was busy starting a new life with that guy she had been sneaking around with he couldn’t help but thinking and even saying out loud to himself.

“I should have married her Mom instead.”

Indeed, the two women did look much like mother and daughter, both of them perky blondes with nice petite figures, and even now in her mid fifties Oliver thought that Pamela Cole was still a very pretty woman with only a few tiny hints that she was actually as old as her driver’s license said.

As Oliver reclined in bed his hand went under the sheets and found his boner, something that had often occurred when he thought about Jill’s mother. He imagined Mrs. Cole’s body was much like her daughter’s, although she had always dressed so modestly he had little to go on but his fantasies.

After stroking his member for a moment Oliver stopped because making a mess like that in the guest bedroom would have been tacky, so he let himself go and tried to go to sleep.

***

The other person in the house, Pamela Cole, was also thinking thoughts she could never admit to having. What she had done with her son-in-law’s clothes before throwing them in the wash disgusted her now that she was in her bedroom, and the idea of Oliver catching her sniffing the crotch of his underwear was too horrible to imagine, but she was so starved for the scent of pheromones that it was as if she had been driven to such a perverse thing.

As Pamela slipped on the bland and shapeless beige nightie and looked at her reflection in the mirror, she grimaced at the way time had taken away her beauty. She was still trim and fit but the way her breasts sagged made her want to cry.

Once they had been perky and firm but as the years went by for whatever reason athe little weight she gained went to her chest and now her breasts hung down to her waist, looking absurd on her skinny frame. That was why she stuffed her bosom in bras she had long ago outgrown in an effort to look as she always had, but when the harness came off – well, it was no secret to Pamela why her husband left her four years ago and why no suitors came rushing to take his place.

As she looked at herself she thought about what she was trying to work up the courage to do. Oliver was in the room across the hall, a very sweet lad who had been crushed when her daughter Jill had dumped him. Maybe he wasn’t the most macho man around, Pamela mused – the term ‘Mama’s boy’ coming to mind – but he was kind and considerate and that had to count for something.

Oliver also had a crush on her. Pamela wasn’t 100% positive about that because it was possible that he was just a very kind man who tried to be nice to his wife’s mother for the sake of his relationship, but the older woman didn’t think so.

What if she did go across the hall? Just for a casual visit of course, but doing so dressed like this was so out of character. Not that the lad would laugh or anything but she still looked nothing like what he had been used to seeing every day for the last few years.

Blame it on the wine. That was what the divorcee told herself as she took a deep breath and went out into the hall, pausing at the door where no light appeared down at the bottom. Maybe he’s asleep, she wondered, and then tapped lightly on the wood, so gently that she might have been subconsciously hoping the knock wasn’t heard.

“Yes Mrs. Cole?” came the voice from inside, causing the woman’s heart to skip a beat, and then she turned the knob and stepped inside the guest room.

***

For a second Oliver thought that he might actually still be asleep because the vision standing in the doorway looked like part of a dream. The dim light coming from the hallway behind her made the little woman look angelic, and not only that it made the image of her body through the nightie rather clear.

“Hope I didn’t wake you Oliver,” his mother-in-law said as she floated towards the bed.

“Me. No. Just thinking Mrs. Cole,” Oliver replied as he tried and failed not to stare at his mother-in-law’s breasts swaying freely under the satin, the size of which shocked him because while he had mentally undressed her many times she had never looked like this in his mind.

“When did you start with the Mrs. Cole nonsense?” she playfully scolded while staying over next to the dresser, aware of Oliver’s gaze and unsure what to do next.

“Well, it’s just that with the divorce coming up,” Oliver mumbled. “I wasn’t sure that…”

“Look honey, you know how I feel about all that, but while I can’t stop any of that from happening the one thing I can do is make sure our relationship stays the same,” Pamela replied as she hoped her stiffening nipples weren’t visible. “I know Jill hates me for what she saw as me taking sides, but I hope we can always remain friends, and I would prefer you call me what you always have – unless you feel you can’t.”

“No. I can. I want to,” Oliver answered, and with a little smile added, “Mom.”

“That’s better,” Pamela responded. “I know you’re probably tired and all but I’m not used to having company these days. Feel like talking a bit?”

“Sure,” Oliver said, and after his mother-in-law looked around for the chair he slid over on the bed and patted the sheet while making she he stayed covered. “Sit down here Mom.”

“Okay son,” Pamela said as she perched on the edge of the mattress and swiveled to face the lad, but when she saw where Oliver continued to stare she felt like a cow and said, “I should go put something on over this. Don’t know why I came in like I am.”

“No, don’t Mom,” Oliver quickly replied and patted her thigh. “I’m sorry to stare but it’s just I can’t believe…”

“I know. It’s no fun getting old. I should have thought twice about what I must look like to a young man like you,” she apologized, although she had thought more than twice and did it anyway.

“That’s not it at all. You look amazing Mrs… I mean Mom,” Oliver said. “Even when we all went to the lake back then you never even wore a bathing suit so I had no idea that – you know – I mean I thought that – you know – because you look a lot alike I figured you were built like Jill.”

“I wish,” Pamela answered, enjoying Oliver’s nervousness which equaled her own.

“No Mom. I mean, you’re voluptuous,” Oliver offered.

“I don’t know about that honey,” Pamela answered, trying to hide the fact that her son-in-law’s words were sending shivers down her spine. “It’s more a case of gravity winning the war.”

“Well, I know you aren’t the type to flaunt yourself, but before when you mentioned that you hadn’t had a date in years?” Oliver noted, and after Pamela nodded he continued. “If you dressed anything like you are now your dance card would be filled.”

“You’re so sweet honey,” Pamela said, the thrill that this seemed to be working making her bold enough to reach over and ruffle her son-in-laws scalp, something she used to do years ago, only now something was different and as she had expected Oliver noticed.

“What’s wrong honey?” Pamela asked, pretending to be unaware that Oliver’s eyes had finally left her breasts and were now fixed on the sparse spray of light brown hair in the deep cavern of her armpit, exposed by the raising of her hand.

“Oh!” Pamela said in what she hoped was a surprised tone. “Guess you know my secret’s out that I’m not a real blonde. Now you and my hairdresser both know. Didn’t mean to gross you out but since there’s nobody around to see it, you know? I can go shave if…”

“NO!” Oliver almost yelled, and after stopping his mother-in-law from leaving he said, “Please don’t. It was just a shock, you know. To be honest all these years I thought that you didn’t have any hair under your arms at all because your armpits were always so silky smooth whenever you would raise your arms.”

“Didn’t know you were checking out my armpits all those years,” she kidded, enjoying him squirm under the sheet before explaining. “That was Jill’s father’s idea. He would throw a fit if I didn’t shave every single day, and even after he left me I kept doing it religiously for a time like the Stepford Wife he always wanted me to be.”

“I guess I shouldn’t say this but, what difference does it make now?” Oliver said. “A few years ago I asked Jill if she would stop shaving under her arms for a while. Just in the winter, because I think it looks sexy on a lot of women.”

“I know,” Pamela admitted. “She told me.”

“She did? Omigod. I’m so embarrassed.”

“Why honey? It’s a harmless thing, and if something so innocuous can make your man happy, I told her to do it,” she explained. “Obviously she didn’t listen to me but back then we communicated at least.

“Can’t believe she told you that though.”

“We used to talk a lot,” Pamela lamented and then added, “If it makes you any less embarrassed, you’re the reason I haven’t shaved in about a month, even since you called and said you would be coming around.”

“Really?”

“Yeah, I thought you might get a kick out of it,” she mused as she lifted her arm again and ran her fingers through the wisp of hair. “Afraid I’m not very hairy these days though. Never did end up with a lot of body hair anyway for whatever reason. Actually I haven’t had to shave my legs at all in years.”

“More information that you were looking for I guess,” Pamela threw in. “Guess I’m so starved for company these days I start talking and can’t seem to shut up.”

“It’s okay. I love hearing you talk,” Oliver assured her. “Jill and I – we haven’t talked much the last year or so, so I guess I miss conversing too.”

“We’re quite a pair you and me kiddo,” Pamela chuckled as she ruffled his hair again. “Only difference is that you’re young and cute so you’ll find somebody else.”

“I doubt it,” Oliver replied, and after thinking for a moment he continued. “Jill – did she happen to tell you why she dumped me?”

“Well, she said stuff,” Pamela responded.

“I mean about my – shortcomings,” Oliver said, nodding downward. “It was why she went looking for somebody better.”

“I don’t think so honey. Jill couldn’t be that shallow.”

“That night we had the argument? When she confessed that she had been seeing another guy for the last few months?” Oliver related as his eyes welled up. “She made a point of telling me about how well endowed he was compared to me. Jill said the guy’s penis was as big as her arm.”

“You know how Jill exaggerates sometimes,” her mother reminded Oliver. “Besides, size is overrated. She just said that to hurt you in the heat of the argument.”

“Well, it worked,” Oliver recalled bitterly. “Even after the fight when I forgave her and we tried to work it out, I couldn’t – you know – perform any more. Despite how small I am I had always been able to – you know – sometimes 3 and 4 times a night! After she told me about that guy, all I could think about was how pathetic I was compared to that guy and I couldn’t – get aroused with her anymore, and if I did manage to get erect I would lose it when Jill would look at my penis. I knew what darn well what she was thinking.”

“I know that virility isn’t a real problem for you,” Pamela answered, and when her son-in-law gave her a questioning look she nodded downward and noted, “Back a few minutes ago when you were looking at me I saw a tent rising in the sheet down there, and please – if it wasn’t there because you were aroused by me just humor me and say it was, okay?”

“No,” Oliver admitted. “It was because of you. I’ve always had a crush on you and seeing you like this…”

“Let me see you,” Pamela asked as she took hold of the sheet, and when Oliver grabbed hold of it his mother-in-law said, “You can’t hide yourself from women the rest of your life, you know?”

“Wanna bet?”

“It’s okay honey,” Pamela cooed softly, and this time when she tugged the sheet down Oliver let go, screwing his eyes shut as the cotton slid down his smooth chest. “We’re just having fun, and that’s something that I haven’t had much of lately. Let’s blame it on the wine, shall we?”

“Honey, you aren’t that small,” Pamela said after exposing her son-in-law’s flaccid penis which laid limply over a pair of healthy sized balls. “You’re not small at all.”

It was only a bit of a white lie on Pamela’s part because although there was no denying that Oliver’s dick was very slender, the uncut organ showed promise of being a respectable length when aroused.

“Really honey,” Pamela assured Oliver after he opened his eyes and met hers. “Although it’s been decades since I saw any but my ex-husband’s, in my day I saw more men’s equipment than I care to admit.”

“As small as mine is?” Oliver asked hopefully. “I mean, I remember in the locker room at school when I would look at other guys…”

“Yes, the same size as yours. Even smaller ones,” Oliver’s mother-in-law lied. “Don’t be scared.”

Those last words were in response to Pamela’s hand landing on Oliver’s scrawny chest, and as her fingers slid downward the lad’s chest heaved wildly, only pausing when her fingernails grazed against the timberline of the patch of dark brown curls above his member.

“Just relax Oliver,” she cooed as her nails raked into the patch of pubic hair, stopping at the base of his penis and then going back up again. “I know this is wrong but…”

“I love you Mom,” Oliver choked as her hand kept playing.

“I love you too son,” Pamela said of the boy she never had, and after letting her hand slide around to cup his wrinkled hairless pouch she kneaded the warm scrotum and noted, “You certainly didn’t get cheated here. Such big balls you have honey. Does this feel good?”

“Yes Mom,” Oliver grunted as he parted his thighs so that the tiny hand holding his jewels had more room to operate.

“I bet that with you and Jill not being together sexually in a while, you have a lot stored up in here,” Pamela noted as her hand rolled the heavy orbs around in her palm.

“Yes Mom,” Oliver grunted.

“Feels nice to touch a man again,” the older woman mused as she rolled the wrinkled sac in her palm, and as she did Oliver’s limp dick, which had been laying in the curls suddenly began to move, getting longer and less wrinkled by the second until it started to rise in small lurches like it was being jacked up.

“Look at you growing. What a beautiful penis you have Oliver,’ Pamela declared at she looked at the pale tube pointing straight up in the air, the 5” or so twitching as it did.

Moving her right hand that was handling his scrotum upwards, she took her wife’s husband’s stalk between her thumb and index finger at the stump while bringing her left hand over and holding the shrouded tip with the same digits of her right hand, slowly peeled the long foreskin down off the taut pink bulb which was drooling pre-cum.

“Oh man!” Oliver whimpered as he watched his mother-in-law move his foreskin up and down over his sensitive glans, the dripping sap moving onto her pale wrinkled fingers.

“You need relief, don’t you Oliver?” Pamela asked.

“Sorry Mom. I can’t hold it back,” the young man grunted as his hand tore at the sheets, and with that the older woman ducked down and took Oliver’s erection in her mouth, her lips barely reaching his pubic hair before jets of his seed began to blast into her throat.

Fighting the urge to choke, Pamela kept swallowing her son-in-law’s forceful ejaculations which seemed to spurt without end, but eventually they stopped and Oliver went limp.

The divorcee kept her daughter’s tool in her mouth for a moment afterwards under raising her mouth off of him, letting her tongue flick at the organ which had retreated into something not much larger than a shell peanut.

“I can’t believe I did that,” Pamela whispered as she wiped the semen off of her mouth and chin. “Please don’t tell Jill if you ever reconcile.”

“Why would I do that?” Oliver asked as his mother-in-law rose from the edge of the bed. “Wait. Mom? Don’t go.”

“I…” Pamela mumbled, shrugging her shoulders as she stood by the side of the bed.

“Please stay,” Oliver practically begged, and when she stood frozen he asked, “Please. Take your nightie off. I want to see you.”

“I can’t,” she said in a quivering voice.

“Yes you can. Let me see how beautiful you are,” Oliver pleaded as the older woman wavered, and then lifted up the bottom of her nightie a little before taking a deep breath and raising it over her head while screwing her eyes shut.

“Knew you’d be beautiful,” her son-in-law sobbed after a moment, and when Pamela opened her eyes she saw her daughter’s husband’s eyes welling up.

“You’ve always been so sweet,” Pamela managed as she looked at Oliver’s reaction which was too honest to be acting.

Pamela didn’t know what he was seeing; surely not her slight paunch practically hidden by her hanging breasts, nor the tiny spider veins visible on her pale thighs or her way her over-sized labia stood out so much through her sparse pubic hair, but for the moment she didn’t care as she climbed back on the bed and knelt beside Oliver.

“Love you so much Mom,” Oliver choked as he tilted his head upward and wrapped his lips around the fat peg of her nipple, almost nursing on the hard bullet while his hands cupped the very spongy flesh.

“Oh, that’s so nice,” Pamela declared as she ran her fingers through her boy’s hair while he suckled on her tender tip, going from breast to breast and even pausing to kiss his way up under her upraised arm to kiss and lick the sweetly scented wisp of hair. “Feels so good.”

“Want to taste you,” Oliver declared and with that he scrambled up to his knees and positioned his mother-in-law on her back, parting her thighs before climbing down between them.

Pamela watched as without hesitation Oliver lowered his head into her delta, most of his face easing between her puffy pussy lips and disappearing into the fold while his tongue went into action.

Every nerve in the middle-aged woman’s body came alive as for the first time in years something besides her fingers entered her sex, and while her son-in-law’s tongue wasn’t as talented as most his enthusiasm made up for it.

“Ooh son!” Pamela moaned as Oliver’s frantic lapping began to have the desired effect, but just as Pamela was about to get close to cumming Oliver stopped, his face rising up from the wet fold. “Don’t stop!”

“Wanna fuck you Mom!” Oliver was saying as he knelt between her thighs, his face red and sweaty, but more importantly, his dick was stiff again and waving in front of him.

“Yes honey,” Pamela heard herself saying as her son-in-law slid effortlessly into her pussy, and as he crouched down and began thrusting hard into her she reached up and wrapped her arms around Oliver’s neck, holding him close while she whispered, “Fuck me son. Fuck me hard.”

The words seemed to send her daughter’s husband into another gear, causing him to hump the middle aged woman like a wild man, the headboard bumping the wall as he went a bit crazy.

Pamela came along the way, her fingernails clawing Oliver’s back as her body shook with pleasure, and when her vision cleared she saw Oliver leaning upward and looking down at her but he was still hard.

“You didn’t cum?” Pamela asked as the young man kept thrusting.

“No. Am I hurting you? Do you want me to stop?” Oliver paused but got a brisk head shake in response.

“No. Don’t stop. Not until you fill me with your seed honey,” Pamela told him as she caressed his cheek sweetly, because while she could hardly feel his modest staff going in and out of her, what she felt was way beyond good. “You’re such a virile man, my son.”

“Do that some more Mom, what you were doing before,” Oliver gasped. “Play with your tits for me.”

“Like this honey?” Pamela asked, not even realizing what she had been doing but understanding, so when her hands went and cupped her doughy breasts which had collapsed onto her he nodded frantically.

“Yeah! That’s it. That’s so sexy!” Oliver cried out as his mother-in-law began kneading the giving flesh and savoring his reaction.

“Oh, your cock feels so good in me,” Pamela moaned as she grabbed her nipples and slowly lifted them upwards while twisting the plump pegs.

“Oh man, that’s incredible!” Oliver almost screamed as he looked down and saw his mother-in-law’s breasts being stretched upwards. “Gonna cum Mom!”

Oliver’s face contorted as he started spurting seed into his mother-in-law’s womb while Pamela smiled and took it with pleasure, and she held him after he was spent, running her fingers through his hair as they caught their breath.

“I hate to do this,” Pamela said after interrupting her son-in-law nursing on her to get up on her knees. “But I have to go.”

“Stay like that for minute Mom,” Oliver asked, and as Pamela froze he grinned as he looked at her sweet hangers swaying down in front of her, the low riding bell-shaped tits looking lush and delicious.

“Omigod. I must look like a cow,” the middle-aged woman said as she wrapped her arm across her chest and hurried to the bathroom. “Gotta go.”

“You could go on me if you want,” Oliver said long after her jiggly butt went around the corner, and as he heard the sounds coming from the bathroom his imagination did the rest.

In his mind Oliver pictured himself on his back next to the bed while his mother-in-law gingerly straddled him, apologizing in saying she never did this before as her sparsely haired pussy opened up above him.

Oliver imagined himself saying that he never had either but had always wondered about it, and that this was like a number of things that Jill would not do or even try, but just before he was about to receive a deluge of both his and her fluids, a voice butted into his mental movie.

“A penny for your thoughts son,” Pamela said as she climbed back onto the bed, but then she burst out in laughter when she saw Oliver had his dick in hand, a penis that was almost erect again. “My word! Are you serious? Are you even human?”

“I was thinking about you Mom,” Oliver admitted as he embraced her. “Thinking about all the things I want to do with you.”

“Well, I suppose I can’t get any more depraved than I am now,” Pamela said. “You know, in my time I was pretty wild.”

“This is your time Mom,” Oliver said. “This is OUR time. Get up for me.”

“Like this?” Pamela asked as she allowed her son-in-law to arrange her so she was on all fours.

“Perfect,” Oliver said as he grabbed the middle-aged woman’s buttocks in his hands, first kneading the spongy flesh and then parting the cheeks to find the brown puckered ring.

“Perfect?” Pamela muttered to herself after glancing upward and turning away after seeing a scary image in the dresser mirror in front of her.

To Pamela there was nothing perfect about seeing herself like this, the silver battling the blonde in her hair as disturbing as seeing her breasts dangling down near the bedding like udders, the bell shaped tits looking like cannonballs stretching out the skin.

“What? What are you doing?” Pamela cried out when she felt something wet licking her anus.

“Eating your ass Mom,” came the muffled voice from below. “If you want me to stop…”

Pamela’s answer was to thrust her backside at her son-in-law’s face, the tip of his tongue popping in and making her yelp while making her forget about what she looked like in the mirror.

“Omigod omigod omigod,” the boy’s mother in law chanted as Oliver orally caressed her anus, the shivering going through her frame only stopping when the lad did.

“Want this so bad,” Oliver said while climbing up to his knees and sliding up to Pamela’s backside, skinning back his foreskin and shoving the tip of his member where his tongue had been.

“Oh yes son. Fuck me in the ass!” Pamela screamed while she saw her almost unrecognizable son-in-law behind her in the mirror, looking like an enraged bull as he bumped into her.

“Take it Mommy!” Oliver yelled, grabbing her scalp gently as he pounded away with quick brisk strokes, and even though his dick barely penetrated her anus when he went forward and popped completely out when he went back, it was good for both of them even though Oliver couldn’t last.

“Oh! Yes! Shot your spunk in there,” Pamela declared as she felt the hot semen cool her. “Yes.”

“I love you so much Mom,” Oliver announced after they collapsed hugging into the bedding.

“I love you too son,” Pamela replied, and although she felt guilty, she also felt like she hadn’t in years.

“Hope I didn’t hurt you Mom. Got a little crazy there.”

“No Son, you didn’t hurt me at all,” Pamela said because the tip of Oliver’s dick tickled more than hurt, but it felt nice and the expression on her son’s face as he took her was even better.

“Mind if I stay for the weekend?” Oliver asked as they cuddled.

“I would love it,” Pamela responded, and was tempted to say that they way she felt at that moment, she might not want him to ever leave.

 

The END.

 

 

2 Comments

  1. As you guys will be aware from my submissions I am a bronze member but my small penis issues are compounded by extreme erectile dysfunction along with premature ejaculation
    I would like to put on record that if it was possible I would happily give up 2 of my 4 3/4 inches and become a gold member if I could perform like this guy in the story
    To be able to get erect and stay erect and make a woman cum so many times without any sign of premature ejaculation is something I dream of

  2. Brings back sexy memories, I was seduced by a good friends mother in law, she called me at work one Saturday afternoon calling herself Mrs Robinson, she asked me round to do something to her car, when I had finished she asked me in, as we sat she said I wonder what it would be like to make love to you.
    Things went from there, although 50 she had a lovely size 10 body with still firm tits, unlike her large daughter whose tits already pointer downwards.
    We made love for what seemed like hours, she never mentioned my small cock, it was hard until twe feel asleep.when we awoke she was studying it,, it was it usual tiny bump but her only question was why was I circumcised? She had never been with a cut guy before , I explained I had had it done about a year ago out of choice and she was the First Lady I had made love to since the cut was done. This aroused us again and we had another session.
    Although she has moved away we still meet up and have sex every few months when she visits my friend and his family.
    Thanks for the story made me very horny about sex with women.

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