Clare looked at the calendar on her messy desktop. It had only been three days since Wesley last visited, but it seemed like a month. And there he was, lying on a lounger, shirtless and showing off that toned and tanned body, no doubt to tease his middle-aged neighbor. And it was working. Despite some residual soreness from the pounding he gave her a few days before, she was ready to get back on that horse, the metaphor being appropriate in more ways than one. The boy was hung like a stallion with a long, meaty cock. .
What the hell. I’ll see if I can arrange a hookup for later on. He looks bored. Clare tweaked a nipple without thinking.
The fifty-year-old MILF stepped out into the sunshine and grabbed a watering can as a pretense for injecting herself into Wes’s day. The teen was lying on a recliner and reading a Sports Illustrated. He looked up and smiled when he saw her approaching him, those big boobs bouncing with each step.
“Hey, neighbor. What’s happening?” Clare busied herself with the watering can and her flowers, casually glancing up from time to time.
“Not much. Just a little light reading. How about you?” Wes was disappointed to see Clare wearing a loose-fitting old man’s shirt. He preferred her in something that accentuated those magnificent breasts, or nothing at all.
“Just keeping the flowers from wilting with a little TLC. Saw you lying here trying to tempt any loose women with your muscles on display. Maybe I should water you. Are you wilting in the heat?”
Clare’s eyes fell to his groin, where the outline of a large tubular shape implied he was not wilting a bit.
“Not that I know of. Need any help with anything, though? I’m available. My folks just left for the weekend. I’ve got the house to myself for a couple of nights.”
Clare perked up at the possibilities presented by this news. Immediately, her brain went into overdrive and other body parts became suddenly moist.
Not really. But I appreciate the offer. If I think of anything, I’ll let you know.
And she did think of something: a surprise. The day couldn’t go by fast enough. Clare even had a glass of wine earlier than her normal late-afternoon happy hour. In fact, she had several. By five, she was ready.
Wes was having a beer since his parents were gone, and watching porn streaming on his laptop when the doorbell rang.
“Fuck! Who could that be?” He quickly closed his computer and hid the beer in the fridge. The antique glass sidelight on the door revealed a woman dressed in a suit, but he couldn’t make out her face. He opened the door, scowling at the inconvenient intrusion.
It took a second for him to recognize this intruder. She was wearing an expensive suit and a tight skirt. Also, she had on a pair of large, black, horn-rimmed glasses. The effect was to make her look like a sexy nerd. Her blonde hair was tied in a prim and proper bun to complete her sterile appearance. But her prominent breasts could not be hidden despite being covered up by the suit jacket. They strained for freedom.
“Oh! Hi, Clare. What’s going on? You’re all dressed up.”
“Hello, Wesley. You can call me Mrs. Hawes. I am the admissions counselor for the college you’ve applied to. I used to be an assistant librarian at your high school, and I taught English electives. Remember? You were so cute. I think I had a little crush on you, even though you never noticed me. I recently started working at the university, so I was excited when I saw your name on the admission list for next fall. We like to do home visits on occasion, and I happened to be in the neighborhood. Is this a bad time?”
“Uh, no! Come on in.” Wes smiled at the obvious role-playing. This should be fun.
“Are your parents home, Wesley? I may need to discuss some things with them.”
“No, they’re gone for a couple of days. Sorry, umm, Mrs. Hawes. You do look familiar. I think I remember you now.”
Wes was excited by what he hoped this might be. His cock was already getting hard as he imagined fucking a nerdy educator with great tits.
“I have some questions for you. It’s better to do this as an interview. Would that be okay?
“Sure. Have a seat.”
Clare sat on the couch. Her tight skirt rode up and exposed her slender thighs and the tops of her nylons. Wes could see a garter strap attached to them. He sat opposite her, relaxed and smiling, and thinking how much fun it would be to see what was hiding under that skirt. He had only seen garter belts in catalogues like Fredericks of Hollywood, but the real thing sent a kinky message to his brain. The look on his face screamed excited anticipation of what was to come.
“I’ll get right to business, then. Wesley, the college has a reputation to maintain. We have high standards and a strict moral code. Incoming freshmen often get the wrong ideas about college freedoms. Some of my questions are sensitive and a bit personal. Some are for statistical purposes only. This is all confidential, of course. Not even your parents will see your responses. Is that okay?
“Sure. Ask away.”
“All right then. First, are you a virgin?”
Wes smiled at the memory of losing his virginity. Clare knew the answer, of course, but he played along.
“No. I lost my virginity some time ago to an older woman, about your age…not that you are old. Sorry.”
“That’s quite all right—no offense taken. I am older. Fifty, actually, although I don’t feel that old. Did you have a positive experience with this woman?”
“Oh, yes. It was very positive. She found out that I have a rather large penis, and she seduced me. She told me it was the best fucking she ever had, even though I felt she was trying to butter me up. I think we both benefited from the experience. As a result, I prefer older women to giggly teenagers. Also, older women don’t seem to be bothered by my penis size. I was always self-conscious about it being so large.
“Interesting.” Clare made notes on a tablet. “Do you have sex often with older women?”
“Not enough, really. I haven’t had sex for several days.”
“I see. Does that frustrate you? Do you masturbate during those gaps, Wesley?”
“Every day.. Sometimes several times in a day.”
Clare’s eyes opened wide at the thought of Wes with his cock in his hand and sperm shooting out of it.
“My goodness. You must have a high sex drive. Would that possibly interfere with your studies? College is very difficult, you know. Your studies will require a great deal of discipline and persistence. Having sex can wear a person out and be a distraction.”
“Oh, no. I can fuck and beat off and still get my work done. In fact, it improves my concentration. I love to masturbate, but I like fucking better, naturally. In fact, this conversation is making me horny just thinking about it.”
Clare squirmed and took on a look of shock when she heard the word ‘fuck” for the second or third time. Wes also noted that her nipples became visible even through her suit jacket when he said he was horny.
“You are very frank for a young man, aren’t you? Do you fuck, as you like to put it, younger women as well? Or just older ladies?” She paused and then dabbed her forehead with a handkerchief from her purse. “Many of our instructors are vulnerable women of an age when sex with students is tempting.”
“No, I’ve only fucked mature women so far. Girls my age haven’t seemed that interested in me, I guess. Of course, that could change in a hurry. Word is getting out about the size of my cock.”
Clare fidgeted and dabbed at her neck with her hanky.
“Yes, you’ve mentioned it is large several times. Wesley, would you mind if I removed my jacket? It seems to be very warm in here.”
“Of course. Where are my manners? Would you like something to drink? Water? A beer?
“Water would be wonderful.”
Wes disappeared into the kitchen and returned moments later with a glass of ice water and his beer. He set them on the coffee table and noticed that Mrs. Hawes had removed her jacket, and the buttons on her blouse strained to hold back the weight of those two beautiful globes he loved to fondle. The top two buttons had been undone, revealing substantial cleavage. Better yet, her hard nipples were now on prominent display even through her support bra and blouse.
“If I may be a little forward, Mrs. Hawes, you have a lovely figure. Are you married? I see a ring.”
“My husband died some time ago. I’m a widow, but I still cherish the thought of him. Hence, the ring.”
“Oh, I’m so sorry.” Wes stood and then moved and sat next to his guest. His arm went around her shoulders, and he hugged her. “That must be terribly difficult for you. The lady who took my virginity had recently lost her husband. I think sex consoled her. She confided that she had missed sex badly with the loss of her husband. She turned out to be a wild fuck. It must be hard to go without sex with the death of a loved one.”
“Yes, it has been difficult. Thank you for your concern. You are very sweet. Back to my questions…you’ve mentioned your large penis several times. If you don’t mind me asking, how large is it?”
“I guess it’s at least a good eight inches long, but I’ve been told it’s also really thick by ladies who should know. i don’t go around comparing myself to others, but I can’t close my fingers around it if it’s hard. Even soft, it’s big. You know, Mrs. Hawes, you are quite pretty, even with your hair in a bun and with those big glasses. I bet you are very lonely without a man in your house any longer.”
A moment passed as Clare looked innocently into her neighbor’s eyes. Neither spoke for several seconds. And then he kissed her. It started as a light, brotherly peck but quickly became an open-mouthed tongue twister. The role-playing was taking on a life of its own.
“Forgive me, Mrs. Hawes, but I just had to kiss you. And I’m going to kiss you again if you don’t mind.”
Mrs. Hawes responded by initiating the kiss on her own. Then she grabbed his hand and placed it on her breast.
“I haven’t been with a man in ages. I have my books and my television for entertainment. I hope I am not being too forward, Wesley, but you have struck a chord in me.”
They embraced, and he was soon on top of her on the couch. Her skirt bunched up, exposing her nylon-covered creamy thighs. Her breasts pressed into him and he worked his hands from them to the hem of her skirt. He worked one hand up the inside of her legs and over her creamy thighs until he realized she wasn’t wearing panties. His hand reached the apex of that junction, and he slipped a finger inside her moist channel. All the while, she was covering him with kisses and moaning. His face bore the marks of her lipstick.
“We shouldn’t be doing this, I know, but I can’t stop. I’m not sure what has come over me. I’m normally very shy. And now, I’m letting a naughty boy put his finger in my most private area, but it feels so good. Maybe I should take off my skirt? This is so nasty. You are really a bad boy, aren’t you? I bet you’d like to put something else in my private places, wouldn’t you? That big penis you are so proud of, hmmm? Okay, I’ll take off my skirt, but you have to promise to look, not touch. Oh, maybe just a little touching. I’m told I have a nice bum.”
She stood and unzipped her skirt before turning around, bending over, and stepping out of it. She unfastened the remaining buttons on her blouse and removed it, but left her sheer bra on, even though her large nipples were clearly visible through the thin fabric. Besides the bra, she was now wearing only a garter belt and sheer nylons. Her blonde pussy hair was neatly trimmed into a two-finger-wide strip. The butterfly wings of her fleshy labia glistened with moisture, and her large clitoris peaked from under its hood of loose skin.
“My goodness. I forgot I wasn’t wearing any panties. What do you think? Do you like garter belts? It’s a throwback to the fifties, and I love that look. I think they’re sexy. Even so, I wasn’t prepared for this. I’m embarrassed to be so brazen with you. Do you think I’m a dirty old lady, especially for a school teacher and librarian?
Wes answered her question with a kiss to her groin. He wasted no time, and as she sat back down next to him, he pushed her back onto the couch and pushed her legs back so her knees were next to her ears. In seconds, he was slowly licking that moist little valley and gently gnawing on her “little man in the canoe.”
“Oh, Wes. Someone taught you well. Yes, that is so naughty. I’ve never had my pussy licked so well, you little devil. If you were my student, I’d keep you after class. Wouldn’t you like to bend your teacher over the desk and put your thing in her from behind? That’s what naughty boys think about, don’t they? I bet you jack off to thoughts like that. And…what is that thing I see growing in your shorts? Are you thinking dirty thoughts? Remember, just looking and a little kissing for now. I’ve never been with a teenage boy before, especially one as naughty as you.
Wes used his tongue as an extra hand and licked Clare judiciously, occasionally inserting it deep in her pink hole. She spread her legs wide to give him complete access. But soon his hands were back at work without complaint, opening her labia wide and fucking her slowly with his fingers. With a free hand, he unzipped his shorts and pulled out his cock with some difficulty. It would not bend to fit through the opening in his underwear, but once out, it looked to be angry.
“My lord, Wes. No wonder older women like you. Probably younger girls also, once they discover that big penis you are packing. That must be the largest penis I’ve ever seen. You weren’t fibbing, were you? Look how big the head is compared to my little hole. I wonder if it would fit inside me. Would you like to see? I’m nice and wet now. But be careful anyway. You are seriously large.”
Wes scooted up so he was on his knees on the floor and gripping the shaft in one hand, he sluiced it up and down Clare’s portal, her large lips folding inward with any effort to enter her. Clare reached down with both hands and spread her labia.
“Try it now. Your penis is so fat it’s going to be a tight fit. There, you’ve got the head in. Look how you are stretching me. This is so exciting, watching your big penis spearing an old teacher’s cunt. That’s what dirty boys call it, don’t they? A cunt. It’s such a nasty word, but it really gets right to the point. That’s it. Fuck your teacher’s cunt, Wesley. I’ve had naughty thoughts, and now you know, I’m a dirty girl, but I love teenagers with big cocks. Oh, Honey. Look, you are almost all the way in. God, that is so hot. You know what would be even better, if you bent me over a desk like we were in a classroom. Do you have a desk? I’ve dreamed about a student doing that to me. I bet you’d love to fuck me that way, wouldn’t you?
Wes was getting into the game now. He added his own version to the role play. He was pounding her with a steady stroke, watching his cock slide in and out of her with those creamy thighs spread wide.
“Sure, Mrs. Hawes. We could go into the den. My dad has a desk there. Just like your old desk at school. most likely.”
Wes slipped his cock out of Clare and stood awkwardly, his cock shiny with their juices and standing straight out. He had to duck-walk before he kicked off his shorts, which were still wrapped around his ankles. He grabbed her hands and pulled her to her feet, and together they walked into his father’s office. The walnut desk top had a few papers on it, but otherwise was clean.
Clare smiled and then kissed Wes briefly as she stroked him, before turning and bending over the desk. She placed her head on the cold wood and watched Wes line up behind her. Her ass was at the perfect height, and Wes slid up to her and rubbed his cock up and down her slit. He hadn’t fucked Clare from behind, and he was amazed at how great her ass looked at fifty. For starters, it was perfectly round and firm, and not very large. Big tits and slim hips. He reached up and unfastened her D cup bra, and Clare raised enough to throw it aside. Her breasts flattened against the desk top when she resumed her previous position. She turned her head to watch as Wes inserted his cock into her beautiful pussy.
From behind, her cunt looked like a ripe peach. Her pussy lips had a hint of moisture, and he marveled at her perfectly trimmed peach fuzz. When Clare felt the fat crown begin to enter her, she spread her legs slightly. She tensed up in anticipation as his thick member buried its full length in her vagina, but first she loosened the comb holding her hair in a tight bun and shook it loose. In an instant, she transformed herself from a prim and proper nerd to a wanton whore.
“Oh, Wesley. I dreamed about fucking you in the library between the stacks. I secretly watched you flirting with girls and used my fingers to get off. Go ahead and do what I fantasized about. I’m a naughty lady. Go ahead and shove that big cock in me. Let me have it. Mmm hmm, yes, just like that. God, you are so thick. That’s it. Fuck me hard; I deserve it.”
Wes grabbed her hips and repeatedly buried his entire length into his neighbor’s pussy. Clare let out a primeval grunt with each stroke as he built up a steady rhythm of fucking her with long strokes. He couldn’t believe the view as he watched his cock glisten with their juices, and her little brown star winked at him. A white coating began to form on his shaft, and he smeared it over his cock and her asshole with his fingers.
“Oh no, Wes. Not in my ass. Your cock is too big. If you want to, you can stick your finger there, but not your big penis. Just get it good and slippery first. I’m a virgin there, at least as far as a penis in my ass. So please…just your finger. Your cock is too big for me there. Maybe another time.”
Clare reached back and spread her cheeks so Wes had a front row seat of his cock working its magic on this sexy librarian. With the addition of his finger in her ass, he could feel his cock worming inside her, separated only by the thin membrane of her perineum. He pulled all the way out occasionally, leaving a gaping maw, and then rammed it to the hilt in a long, smooth stroke. His entire shaft was now covered in a copious, milky goo from Clare’s vagina. Each thrust resulted in a squishy, slapping sound as his groin met her rippling ass with a smack.
“That’s it. Fuck me like I deserve to be fucked. When you cum, you can cum on my face if you want. Or in my creamy pussy. Either way. I love both the taste and feel of cum. I bet you cum a lot, don’t you? You are so hard.”
Wes imagined his teacher taking a load on her face, and it was too much. He stroked her furiously several more times and then pulled out quickly. Clare spun around and faced him as the first spurt striped her face, covering one lens of her glasses and her forehead in a thick stream of cum. Several more followed, covering her face and open mouth, eventually dripping onto her now bared breasts.
When his cock began to soften, Clare gripped the shaft and, stretching her lips wide, put the head into her mouth and gently sucked. Her face looked like she had lost a hands-free banana cream pie eating contest. She giggled and wiped a gob off her cheek and then inserted it in her mouth.
“God, that was so hot!” Wes looked like he had just won the lottery. And, really…he had.
In time, they returned to the couch and eventually got dressed. Clare waited until it was dark before returning to her house. She fixed a TV dinner and ended up going to bed early. As she was ready to turn out the light, her phone pinged. A text scrolled across the screen from Wes.
“Mrs. Hawes. You are my favorite teacher.”
Seconds later, he received a reply.
“Would you like to tuck me in? My door is unlocked.”
