Wife's Mom, Sister & Best Friend Ch. 01

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Wife's Mother, Sister & Best Friend

Chapter Two -- Roger has sex with his mother-in-law, Gertrude

Roger has sex with his wife's mother, his MILF of a mother-in-law, Gertrude or Trudy, as she prefers being called.

Gertrude, or Trudy, as she preferred being called is a beautiful woman. With them born only a year apart, she could have been Christie Brinkley's Irish, twin sister. A classic, blonde bombshell with long, shapely legs, she was as beautiful as her two daughters, Gwen, his wife, and Genevieve, his sister-in-law. Even though Trudy was a 60-year-old woman, looking ten years younger, she was just as beautiful and as sexually desirable as Gwen's best friend, Heather. As much as Roger loved having sex with his wife, an understatement, he loved having sex with her mother too, not to mention him having sex with her sister and best friend wasn't so bad either.

Nearly as forbidden as him having sex with his own mother, there was just something so intoxicatingly forbidden when having sex with his mother-in-law that drove him wild. With him going from one woman to the other woman while making sexual, physical, and emotional comparisons as he went, there was just something so erotically exciting in having sex with both mother and daughter. With him a lucky man having already possessed that knowledge, he already knew what it would be like having sex with Gwen twenty years from now. After being sexually intimate with her mother so very many times and with Gwen and her mother so very much alike, if having sex with Gwen twenty years from now was anything like having sex with her mother now, then he'd never have to wonder. Moreover, he'd be a happy man.

Roger was well aware that his wife was a very sound sleeper, especially after taking her sleeping pill. If ever there was a fire, unable to roust her, he'd have to carry her down the stairs and out of the house unconscious. With her sleeping like the dead, he was hidden from detection with the help of her sleeping pill, sleeping mask, and earplugs. Concealed within the cloak of darkness of the bedroom, every Monday and Thursday night, Roger allowed his mother-in-law access to his bedroom and to his bed.

Tuesday and Friday nights was Genevieve's turn to have sex with her brother-in-law and Wednesday and Sunday nights was Heather's turn to have sex with her best friend's husband. Only now, with his change in work schedule, according to what Trudy told him in the garage this morning, he'll be having sex with his MILF of a mother-in-law, his sexy sister-in-law, and his wife's hot, best friend every night. One at a time, every night the three women would be in his bedroom and in his bed. Every night, he'll be having sex with his mother-in-law, sister-in-law, and wife's best friend.

Light afoot, arriving in a nearly silent whoosh, as if she was a ghost or an enchanted fairy arriving in his sleeping chambers through a secret door, always so quiet, Trudy crept in without making a sound. As much as he didn't want to awaken his wife, she obviously didn't want to awaken her daughter. With her familiar with her daughter's darkened bedroom, Gwen's mother made her way through the total darkness without bumping into anything and/or injuring herself.

"Hi Roger," she said whispering her greeting to her son-in-law in the darkness with a hug and a kiss.

"Hi Mom," said Roger returning her whispered greeting with a hug and a kiss.

Just as there was something so sexually exciting about having sex with his mother-in-law, there was something so intoxicatingly erotica and dangerously naughty about having sex with Trudy when Gwen was there in the room and in bed with them. If ever Gwen caught him with her mother, her sister, and/or her best friend, he'd have Hell to pay. He could only imagine how she'd react. To say that she'd be angry is a huge understatement.

"You had sex with my mother? You had sex with my sister? You had sex with my best friend? What's wrong with you? And this has been going on for how long? You've been having sex with them for fifteen years, as long as we've been married? Oh, my God! How could you? Oh, my God! How dare you? We're done. We're through. We're finished. This marriage is over. I want a divorce. Get out! Get out of my bedroom. Get out! Get out of my house. Go! Take your things and go!"

With her violent temper and with him not wanting to unleash the beast of his sometimes shrew of a wife, he could only imagine her reaction if she ever knew he's been having sex with her mother, her sister, and her best friend. Not a total fool, he removed the bullets from his handgun and hid them. Having no other choice than to have sex with her mother, her sister, and her best friend in his bedroom while his wife slept, he prayed that she'd stay sleeping and fortunately for him, always she did. Not wanting to hurt her feelings, not wanting to start a fight, and not wanting to throw him out of the house, and ask for a divorce, he hoped she'd remain fast asleep until they were all done having sex.

As soon as Trudy made her way to his side of the bed, she scooted in beside him.

"How are you baby? I missed you," she said.

A term of endearment, from the time he was dating her daughter, she insisted that he call her Mom instead of Gertrude or Trudy.

"I'm good," he said in her ear. "I missed you too, Mom."

Then, hugging him and cuddling with him beneath the covers, she kissed him as if they were on their Honeymoon, albeit with his wifely chaperone next to him. Roger always kissed his mother-in-law as if this was the first time French kissing his wife's mother. His very favorite thing to do, he kissed her while touching and feeling her through her clothes. Instead of coming to him in her nightgown as Genevieve did or naked as Heather always has, Trudy came to him fully dressed.

In the way of which comes first the chicken or the egg, he didn't know which sexually aroused him more, French kissing his mother-in-law or feeling her through her clothes. Actually kissing her while feeling her through her clothes was by far more sexually exciting than one without the other. In the scheme of things, he didn't have much time to have sex with the three women and he needed to conserve his energy and to save enough time for Genevieve and Heather too. Yet, taking his sweet time with Trudy, every time having sex with Gwen's mother was a special occasion and was as if it this was their first time having sex with her.

"God you have such big tits, Mom," he said whispering the same thing to her every time and with her swooning every time he said it.

He loved feeling her huge breasts through her blouse and bra while fingering her emerging nipples.

"I'm glad you like my breasts Roger," whispered Trudy. "I've always loved feeling your hands all over me."

Overflowing her bra cups, Trudy has huge, firm breasts, a D cup that looked and felt more like a double D cup. Where both her daughters have shapely C cup breasts that will surely grow to be D cup breasts as they age and put on a few pounds, Roger loved big breasted women. Even Heather had beautiful, firm, and shapely, C cup breasts. Yet, Trudy's tits, so shapely, so round and so firm, were special. With her well preserved from diet, exercise, and limited exposure from the sun, she had the breasts more of a forty-year-old woman than a sixty-year-old woman.

Even more than he loved the sensation of feeling her huge breasts through her blouse and bra while kissing and kissing her, he loved the sensation of mashing his face in her naked tits while fingering and sucking her nipples. Much more sexually exciting than feeling, fondling, and sucking the tits of an older woman, a cougar of a woman, the fact that Trudy was his mother-in-law made having sex with her much more sexually arousing. Not all one way in their lovemaking, his mother-in-law seemingly enjoyed feeling his erection through his pajama bottoms while making out with him too.

"Someone is horny," she whispered sticking her hand inside of his pajama bottoms and wrapping her soft hand around his hard cock. "You must be happy to see me," she said with a sexy albeit dirty laugh.

He smiled at her in the darkness.

"You never fail to give me an erection," he said whispering his lust for her in her ear. "I can't wait for you to suck me. I can't wait to cum in your mouth Mom," he said slowly sliding his finger along his mother-in-law's lips.

She gave him a sexy look that he could see even in the dark. Then, in the way she'd soon be taking his stiff prick in her mouth, she took his finger in her mouth and licked it before sucking it while staring up at him in the dark.

"You make my nipples so big. I can't wait for you to suck my tits," she said.

With her just as horny as he was, fortunately for him, his mother-in-law, sister-in-law, and wife's best friend were all just as horny as his wife. Trudy's hands were all over his naked cock and testicles in the way that his hands were all over her blouse and bra clad breasts and protruding nipples. Strictly forbidden within the conforming constraints of normal, modern society within puritanical America, what made their sexual union so special was that Trudy was Gwen's mother and he was her son-in-law.

For sure, he wouldn't feel as sexually excited if she was just some older woman that he picked up in a bar. With many men having the sexual fantasies of having sex with a mother-in-law who looks like her, his sexual fantasy come true, this was his MILF of a mother-in-law that he had next to him in bed. Tonight was the night. Not only was he going to have sex with his mother-in-law but also he was going to have sex with his sister-in-law and his wife's best friend. A first time for everything, he's never had sex with all three women in one night, albeit individually.

Slowly and excitedly, as if this was the first time seeing her huge breasts, he unbuttoned one slow button of her white blouse at a time while looking down to see what each unbuttoned button revealed. Touching the tops of her meaty breasts and feeling her huge tits through her bra, he fingered and coaxed out the hard, erect impressions of her nipples through her low cut, sexy brassiere. When her blouse was finally all unbuttoned, he flayed open her shirt to stare at her abundant bra clad breasts and her long line of cleavage. She had such huge breasts and sexy cleavage.

He teased her by seducing her breasts with his long, stiff finger, as if his finger was his cock and her cleavage was her pussy slit. As if traversing a double sided highway and taking a detour over her nipples that pushed out through her bra, probing her deeper, he traced her long, sexy line of cleavage with his finger. As if her breasts were two mountains and her cleavage was a narrow mountain pass that promised a glorious view at the end, on the chance his finger would be crushed by her huge breasts, he forced his finger deeper between her big boobs. In and out, as if fucking her pussy with his cock, he fucked her cleavage with his finger.

"Oh, my God. I just love your huge tits Trudy," he said quietly enough for Gwen not to hear.

She looked down to watch his finger having sex with her cleavage.

"I like what you're doing with your finger. Keep on doing that," she said whispering in his ear while kissing and licking his ear. "Fuck my tits with your long, thick finger. That makes me so hot."

As if her cleavage was her pussy slit, whenever he fucked her cleavage with his finger, she always let out a nearly silent, little gasp. While he depressed each side of her magnificent breasts with his finger, she obviously enjoyed it when he seduced her cleavage with his index finger as much as he enjoyed it when he fucked her cleavage with his finger or with his cock. Seemingly she enjoyed him forcing her breast apart with his finger nearly as much as he enjoyed forcing her breasts apart with his finger and nearly as much as she enjoyed him forcing her pussy lips apart with his finger.

In the way that he enjoyed feeling her breasts through her blouse and bra while kissing her, he enjoyed feeling her huge breasts and hard, erect nipples through her bra too. Cupping them while squeezing her huge, bra clad tits in his hands, it didn't take very long for her big nipples to show her sexual excitement by the hard impressions they made through her bra. Sucking and nibbling on her big nipples through her bra was one of his favorite things to do and in the sexually excited way that she squirmed her appreciation for the sexual attention he paid to her breasts and nipples with his mouth, she enjoyed his mouth too.

All part of who his mother-in-law was, a beautiful blonde with huge breasts, he loved her big nipples as much as he loved her huge tits. In the way that so very many women have breast implants and breast augmentation surgery, Trudy didn't need the help of a plastic surgeon to look better and shapelier in her clothes. A gift from God that wasn't manmade, born with them, her super big breasts were all natural.

As if he had taken her parking after a date, feeling her ass through her short skirt and her pussy through her panty, he never stopped kissing her and he never stopped touching and feeling her through her clothes. He continued French kissing her while feeling her big boobs with one hand and fingering her pussy through her panty with his other hand. Not allowing him to have all of the fun, Trudy already had her horny hand inside of his pajama bottoms and around his cock. As if she was holding her dildo or her personal pull toy, she held his hard cock in her soft hand while fondling the head of his engorged prick with her manicured fingers. Then, as if there was a drumroll of sexual suspense and with the alarms of erotic anticipation going off in his head, he helped her off with her blouse before he reached around behind her to unhook her bra.

In the way of a skilled, albeit blind safecracker who didn't need the assistance of a light to see what he was deftly doing, his fingers felt her bra hooks while he listened for the clicks. One handed, he unhooked all four of her bra hooks. Then, as if there was something valuable hidden inside and there was, as if unveiling a work of art, a masterpiece, he took his time in revealing the artistic display of her hidden, mountainous treasures. Slowly, with great sexual anticipation, he peeled her bra straps from her shoulders, first one and then the other. Finally, removing one, slow, bra cup at a time, with him always acting as if this was the first time seeing her naked breasts, he removed her bra.

Always he stared at her huge breasts and erect nipples before touching them, feeling them, and fondling them. Then touching her naked breasts, feeling her firm tits, and fondling her huge tits, he fingered her nipples. Trudy wasn't just any woman, she was his wife's mother, his mother-in-law, and here she was with him in his bed topless. With the twin peak playground now open, and with his mother-in-law's naked fun bags totally exposed to his horny eyes, hands, fingers, and mouth, he enjoyed the majestic view of her huge breasts even in the dark.

Already erect and hardened by her sexual arousal, her nipples begged to be fingered and sucked, and he obliged her. As if she was breast feeding him, he could never resist sucking her huge tits. First, while continuing to kiss and kiss her, he felt and fondled her huge breasts while fingering her big nipples. Then, while still kissing and kissing her, he fingered, pulled, turned, and twisted her enormous nipples. Always his favorite part of having his wicked, sexual way with Trudy's big tits, he couldn't wait to suck them.

"I can't get enough of your huge breasts Trudy. I love sucking your nipples," he said.

She looked down at him sucking her tits as if she was breast feeding her baby.

"Suck my nipples Roger. Suck them. Bite them. Turn them, twist them, and pull them," she said. "Squeeze my tits. Harder. Squeeze them harder. You won't hurt me. Oh, my God, I love the way you're so sexually enamored with my breasts."

First one and then the other, he took her big tits in his mouth to suck, nibble, and bite her nipples while squeezing her massive breasts. It always so excited him that he was sucking the tits of Gwen's mother while his wife was asleep beside him. Seemingly in age, maturity, respect, and authority, with her one step away from his own mother, there was just something so erotically sexual about him touching, feeling, fondling, and sucking his mother-in-law's tits. Just as there was something so erotically sexual about having his wicked way with her naked breasts, there was something equally as erotic with her having her wicked way with his naked cock.

"I can't wait to lick your pussy. I can't wait to make you cum," whispered Roger while sliding down her voluptuous body and staring up at her pretty face.

Not wasting any time in making oral love to his mother-in-law, Roger stopped sucking Trudy's tits to position himself between her shapely legs. With her thighs firm from doing Pilate's exercises and her calves muscled from jogging, she had great legs for a mature woman. Again, as if unveiling a hidden treasure, he pushed up her short skirt to her waist to reveal her bright, white cotton panty. Then, as if he was her gynecologist examining her with not only his finger but also with his tongue, she lifted her shapely butt for him to remove her panty. Licking her while fingering her blonde, bushy pussy, as he's done so very many times before, sticking his fingers along with his tongue inside of her pussy, he was intent on giving her an oral orgasm.

"Oh my God, Roger, rub my clit while licking my pussy. Eat me. Rub me harder while licking me faster," she said running her fingers through his dark, chestnut brown hair.

In the way he put a gentle hand to her blonde, pretty head when she's sucking his cock, she put a hand to the back of his head to mash his face in her wet cunt. Obeying her in the way that any son-in-law would obey his mother-in-law, he gave her what she so wanted now, an oral orgasm, in anticipation of her giving him what he so wanted later, a blowjob. He buried his nose in her bushy mound to get a whiff of the muskiness of her sexual aroma. Mashing his face in her pussy in the way that he enjoys mashing his face in her naked breasts, he had her vaginal secretions in his mouth, up his nose, and all over his face.

With him experienced eating his mother-in-law enough to make her cum within only a few minutes, wanting to taste her, he wanted her to cum in his mouth. Sexually exciting to give his wife's mother oral sex, in the way that he loved eating Gwen and Heather, he loved eating Trudy's bushy, blonde pussy too. He loved eating his mother-in-law as much as he loved eating his wife and her best friend, Heather.

Unlike her mother and Gwen's best friend, Gwen's sister, Genevieve, would much rather that Roger fuck her pussy than to eat her pussy. She'd much rather fuck than to be eaten. She'd much rather fuck than to suck but after he gave Gwen's sister what she wanted, a good hard fucking, she gave him what he wanted too, a blowjob that culminated in cumming in her mouth and her swallowing his cum. Genevieve was the wild woman of the three.

"I love licking your cunt Mom," said Roger knowing that Trudy got off when he talked dirty.

He loved feeling Trudy silently move the more she became sexually aroused. When she closed her legs around his head to block his ears with her thighs, it was a special sensation as if she was birthing him. With his fingers and tongue deep within her, and with her moving and softly moaning to his sexual touches, he felt so very close to her. As soon as she stretched out and stiffened her legs, licking her faster while fingering her deeper, he knew she was ready to cum.