7 More MILF Stories

by Sophie Sin

  “No idea, sir.”

  He sighs.

  “Alright then. Tell Gemma that I need to see her about her tuition when you talk to her next.”

  The older man strolls off. I lean against the wall. That was too fucking close. Seriously...

  Choosing A Woman

  Frank Henderson, being sympathetic but firm

  Two months have passed since the first time that I had sex with her mother and sadly it's become apparent that I have to break up with the young woman as she just can't compete.

  “I'm sorry. The spark left some time ago, but I didn't want to say anything.”

  Gemma's tears stain my dark green shirt's shoulder. The small family owned cafe we are in is quiet. The background music to our little drama is low tempo music and the room virtually wreaks of brewed coffee from the several drip machines the line one wall.

  I pat her back and assure her everything is going to be okay for the third time since I told her that it is all over.

  25 minutes later I leave through the front door, the bells above it chiming on my leaving, and pad down the street in the light heat of this late autumn day.

  For a second I glance back at the cafe receding in the background. That went better than expected, but 'better' is quite subjective when one is talking about a break up.

  A flush of autumn chill runs over me as I stroll down the street. Beside me a black convertible with the top rolled up slides to a slow halt.

  “Well if it isn't young Brad.”

  Mrs. Johns will never learn my name. I'm certain of it.

  “I broke it off,” I say.

  “And? You'll never have me.”

  “I know.” Why deny the truth? No one can catch the heart of a woman that believes that deviousness is the primary quality that all women should uphold and practice regularly. She may not be evil, but temptation is her bliss.

  “Do you have the martini mix at your apartment that I asked for?” she asks, leaning out the window a little to intentionally flash me some of her cleavage as she looks up at me.

  “Yes, ma'am.”

  Her grin is wider than usual.

  “Then I'll be coming over for a drink.”

  I shake my head. This woman is trouble, but, then again, I think I'm starting to like trouble and trouble with big breasts is even better I've found.

  “Can I get a lift?”

  “Only if you're good.”

  She pops the door and I get into the plush interior. Her hand is on my thigh and traveling inward before we make it 20 meters down the road.

  “You will be a good boy for me, won't you, Micheal?”

  I ignore her little attempt at teasing me. “Yes, ma'am.”

  And that, folks, is how a MILF seduces her daughter's boyfriend. I'm glad I was in the position to be him.

  An Orchard Of Older Love

  More MILF Series

  Her fingers lightly bristle over the sun-kissed sharpness of the leaves on a fat branch in front of her. They caress down the bark and come to two golden ripe apples. Mrs. Column's index finger swirls around on the soft flesh of each slowly and delicately. Then her eyes turn to me. An older woman, an lonely orchard and a younger man who is old enough to know better. Love doesn't need the boundaries of four walls.

  In The Orchard With Mrs. Column

  Her fingers brush along a brace of apples hanging lightly from a nearby tree with the grace of a woman much younger than her in their years.

  Mary Column, my mother's friend, 43 years of age – beautiful: A rose still firmly in its bloom – and mine.

  “Do you feel the warmth of the sun today?” she asks

  My eyes meet her blue jewels. They twinkle with mirth and excitement. I know what she is suggesting.

  “You want to sun bathe?”

  “Not exactly, Kieth,“ she purrs, her nimble feet taking her to me and her lips to mine for longer than I'm willing to admit as being chaste.

  “Mrs Column, is that really how you should be kissing your friend's son?”

  Her warm chuckle is music to my ears. One hand comes up and runs slowly through my brown mousy hair.

  “I think you are more than just Judith's son to me, don't you?”

  “And how would Mr. Column feel about that?”

  There is a faint crinkling around her eyes. That playful look hasn't disappeared from them. If anything it has become stronger and brighter and far more arousing in the quality of its mirth.

  “Who said that he has to know? The springtime of a man's youth only comes once.”

  Her hand strays low on my stomach.

  “Doesn't it?”

  I groan as that hand runs down and under the waist band of my shorts and into the place where I know that – for all my best efforts to stop myself – I should not be letting her go. Mrs. Column is married after all; not some single girl of 25 with nothing to lose, but a woman with a young son of 17 and one of 12, yet still more beautiful than any other woman that I have ever seen: The stuff of dreams given two hands and two feet to please and pleasure (with a wonderful array of other gorgeous points between each.)

  I moan in pleasure as her small fingers cup my balls and roll them around in light little tickling circles. Always this moment – that first touch of her body, sexy and desiring against my own – reminds me that she is no inexperienced girl. This is a professional, someone who has honed their skills in the bedroom to perfection, and, of course, I know that skill has to have come from somewhere. Mrs. Column has had men and I am only one, but each time she manages to make it special. I honestly believe that she would to do more for me than any other man that she has been with, but that is perhaps just the vibe that she gives off. I am not sure if what I believe is a falsity of her charm or reality as it is.

  The woman's lips are as nimble as her feet were before as they shifted across the grass that sits among the rows of the orchard that we stole into when the farmer and his work hands were not about. My mind is only vaguely aware that being caught here like this, with Mrs. Column on her knees and my harden manhood sticking so far out in its erectness as to scare me and concern me that it might snap something inside with how hard it has become, is dangerous. For me this is all about what I would lose after we were caught, not what would happen when caught. Hence, I am careful in my cries.

  Mrs. Column draws back the foreskin and licks very slowly and carefully around the pink inside. Each little bit of lubrication sends a shiver through my body as she works the skin back over the edge of the knob and gives her attention to the eye at the end, which, with a pressing of her fingers, opens widely and accepts her tongue – only a millimeter of it but enough to make me stand up on my toes and bless the sun (our only companion in this act of gratification in our outdoor environment) with my upward tilted jaw and strong cry.

  “It's dirty!” I whine.

  Dirty does not faze Mrs. Column. She is not one – in my experience – to be thrown aside by something unclean.

  “Turn,” is all that she offers.

  I hustle about and cry out as her tongue, that wicked item of flesh, is slowly pressed between my butt cheeks, working over either side and leaving a long wet trail of saliva, before working upwards to the hole and tickling the flesh before sliding inside.

  “Noooo...” I whine, “this is too much.”

  'Too much' are two words that I should never think to utter with this woman. Every time I think there's a limit to how far she can go and how far she can take me down the dark path of mature sexual adulthood, she takes me further. It's like there's always a new dark tunnel that I don't know about and she, the guide, is the one in charge of pushing me down it kicking and screaming to something new and even more erotic. Sex with Mrs. Column will never get old, even if she does.

  I place my hands in the branches and feel their hard barky coating. An apple falls with a plonk as my fingers tear at the leaves on what is in front of me. The rustling of these leaves, the breeze running through them, and the sweat pouring from my bro
w, even though it is not quite that hot, are like hot elixir poured all over me. My dick, which is now being caressed in both of her hands, is straining at the bit. I will cum soon and that would be a great shame, because, due to our friendly breeze, I can smell that she is quite wet. No point in wasting a wet load on a green grassy area when there is a wet pussy to dump it in. No point at all.

  My affections are rough and rousing as they usually are. Mrs. Column has chastised me many times for being such a hasty lover – her point being that the other women that I will meet might not find such a youthful effort to be pleasing. I don't feel that she is correct in this case. It is only her that can turn me into a raving sex maniac and today I am more on the edge that usual.

  First, I take her dress, pull it down and expose the tanned flesh of her huge breasts. These have been suckled by two children, but they know a man's touch and the difference between it and a child's. I run my fingers over the skin before – unable to restrain myself – I partake of her sexy, tight nipples that burst to life under my thick tongue and bristled chin.

  “Oh, Keith!” My name from her lips is pleasure enough to make me ravage her even further. I take both nipples and yank them out long and strong before bringing them together

  It always surprises me how flexible a mature woman's nipples can be. They reach together and I can get them between my teeth to nibble and suckle just as she likes it.

  The woman's moans are rich in that sharp soft tone of her voice. I work her breasts until I can handle no more. Already my hands have been working my cock long and strong and it is time to take the prize. I can wait no longer.

  Turning her and pulling up the autumn blue dress that is one season too early, I bend her at the hips, take one long good look at the bare big behind that I have for my play today and insert my dick to the end of its extent into her rich and warm pussy.

  “Ahhhh!”

  Her moan is loud and might arouse some suspicion if someone were to hear it, but I treasure that sound. This is her at her best. Outdoors, half naked, a younger man's cock in her pussy and her husband nowhere to be seen. This is Mrs. Column and god is she sexy.

  I take her rear in both hands as she grabs a hold of some of the branches, more apples clonking to the ground, and begin my assault.

  At first I was gentle with her in our love making when we first met, but after a period where she would not return my phone calls I realized that hard is best in keeping an older woman. Her body is not as sensitive as a younger, less stretched and untrained younger woman might be. In this case it is a wide hole I find under my dick, but that is fine as well. I'm not a small man and I prefer someone who wouldn't complain if I want to really hurt her pussy in our play.

  Mrs. Column continues her moaning. I reach around and stick my fingers into her mouth to dull the sound and enjoy the soft smooth feel of her saliva on my fingertips as she suckles them as I fuck her rear.

  Harder. Harder. Harder.

  Always I want harder with Mrs. Columns.

  An older woman.

  One like this.

  She can take a lot of pounding and today is no exception.

  I ram into her so strongly the the tree shakes violently. She can barely stand, but I hold back nothing. 200 strokes or more later, her pussy clenches, ejects me and squirts a faint semen colored juice from the hole. This is not her squirting, but my cum being pushed out. It was only yesterday that I filled her womanhood up and now she is rejecting that sperm? I will have to do something about that.

  Forcing myself back in, I take that softness as her back arches and her legs tense and her words beg for me to finish inside.

  It is not long before I do. My juices pour into her womb once more and take their rightful place in her vagina. The seat of my power over her has been regained. I would prefer it no other way.

  “Apple?” she asks after her breath has recovered.

  I pick up one of the dozens that have fallen from the tree and hand her another.

  We take a bite.

  “Sweet as sex on a warm sunny day.”

  Mrs. Column smirks at me.

  “Sweeter.”

  DOUBLE BACK: Two To Rear

  Sophie Sin's Classics #2

  This is a part of Sophie Sin's Classics and, therefore, one of Sophie's older books.

  What A Girl Thinks About When...

  Sarah looked into the mirror admiring how the light glimmered off the glittery foundation that covered her entire body giving the illusion that her skin glowed more than a girl in her early 20s should. She brought her hands around her firm, muscular belly to run up to her rounded mounds.

  Her nipples were already peaked thinking about what she was getting paid to do for the next 24 hours. Rick and Tim were her favorite customers. They paid big, $5000 each big, to enjoy her services unprotected and illicit for the evening. The money was going to pay the rent for a very long time once they got finished fucking her brains out.

  That was what she really, really loved about those two. These weren’t fly by night pinheads who cruised Thailand for the type of sex she offered. These were all American sex machines that only dipped their wicks when the quality of the pudding was at the highest standard.

  She reached down and gave herself a little twirl. Already her clit was standing on end and burning red with blood. It was hard not to touch herself on a Rick and Tim night. This was her 12th time enjoying the gentlemen’s attention and she had high hopes. Good quality sex was only a half hour away.

  She’d been slumming a bit lately with clean, but low quality men that paid well, didn’t have any diseases as far as the checks went, but didn’t know how to stir a girl up inside. She had waited through all the trash and now she was returning to the Garden of Eden to feast on the apples, or in the case of these two: A double cream pie wherever they wanted to put it.

  She put on her bra and panties, ensuring that everything was perfect and that not a lock of her golden brown hair was out of place. She looked like a super model and that was what the boys paid for. Quality was all about appearance… she rubbed herself again… and a tight twat.

  *****

  The car picked her up at the appointed time. The agency was always on time. They took 30% of her pay for the pleasure of setting up the meets and making sure everyone was clean. Sarah was on the ‘special’ list, which meant she only fulfilled special needs, for special men, in the places of their choice.

  Unprotected sex was dangerous, but she figured that if she was a regular whore working the block then she would have caught much worse. The men she were with didn’t usually slum low enough to catch anything and there were checks. She would be safe.

  They pulled up outside of one of Rick’s ‘city homes’. The man had so much money that he no longer had to work if he wished. He had once told her the sum. It had enough zeros to make him a prize catch for any girl with the smarts to pull him in.

  She smiled again. She didn’t want to marry him. She was here for his cock.

  She got out and walked up the stairs. Her heels weren’t really made for steps, so she wobbled about drunkenly.

  The door opened at the top and Rick stood in all his glory waiting for her. 6ft of raw male muscle: The man spent all his time fucking and working out. He was a stallion among draft horses. She felt a warm tingle surging up through her feet towards her groin. He had that affect on her.

  “You look sexy,” he said looking her hard in the eyes.

  She went a little weak in the knees looking into those brown eyes. He was a real man, not some half-ass little boy pretending she was a pony in need of riding. He was going to shake and bake her vagina violently.

  She stepped inside and found Tim standing at the top of the stairs. If Rick was all masculine power, Tim was wily sexiness. He was almost beautiful enough to be a woman.

  Sarah was thankful that he wasn’t. She could see the outline of his 9inch jack hammer through his pants, which was thick enough to make only the biggest of condoms usable.


  He strolled down stairs and kissed her on the lips. Rick came up behind her and started fiddling with her dress.

  “Here?” she asked.

  Rick smiled and dropped the dress to the floor. She stepped out of it and spread her legs wide.

  Tim got down on his knees and dropped her panties down to her knees. His 9inch cock was big, but the man also had one of the most phenomenal tongues she had ever come across on the block or off. He was a pro in every way shape and form.

  Rick dropped her bra to the floor and came around to settle in on her breasts. She watched his eyes take in the view. It always made her worry a little when he looked at them. Her breasts where big, but Rick had a strong tit fetish. Was he seeing something mediocre or was he satisfied?

  He cupped them with his powerful hands. His strength and technique were perfect. Just with this little massage, the feeling in her crouch as Tim went to work taking her to seventh heaven increased sevenfold. He was a master.

  Tim rotated his tongue around her clit slowly. She could feel him considering his approach with that firm tongue of his. She was hoping for a bit of a release, but drawing it out was also quite nice. She was undecided about, which option suited her best. To cum or not to cum?

  He went for the direct approach and stuck three fingers in. She always made sure that she was stretched and ready. It had been awhile since one or even two fingers were enough to sate her thirsty crack. Tim knew she would want the whole hand by the end of tonight.

  He inserted and began the inward outward movement that made her oh so happy that she had gotten these two men tonight. He worked her, twisting, turning, screwing her puss.

  Sarah groaned and came forward against Rick’s firm sexy arms. He pushed her up and brought his mouth to hers. Their tongues went around and around as Tim’s fingers went around and around below. She was spinning in a soup pot of happy feelings.