Craig's List Whore

Story Info
The story of a recent Craig's List hook up.
2.4k words
4.44
17.3k
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Whore!" My eyes skim over the emailed reply. It doesn't hurt my feelings. I've accepted what I am. I understand few "real" women look to Craigslist to find sex partners. Even fewer do multiple times. I'd try to convince you my situation was unique, but in truth you hear some variation of it all the time; in a sexless marriage, frustrated, unsatisfied. My marriage isn't loveless though and I'm not trapped. I adore my husband and he spoils me in countless ways, just not sexually- not because he doesn't want to but because he can't. Diabetes took away his function. Medications for complications dimmed his drive.

Do I feel guilty? Yes, I do. Not for my sexuality, but for the dishonestly. In my dream world his cock would get hard and he'd be horny as hell and my sexcapades would include him, along with some other players that he willingly shared me with. I'd be fair about it though. I'm ok if he fucks others too. I'm secure enough to get turned on watching another woman suck him off, but alas that isn't an option.

And I did try to behave. I tried so hard. Months and even years went by with masturbation serving as my means for orgasm. Recently though for some reason, I get almost insanely horny. I'm turning 45 soon and questioning if this is what is meant by a sexual peak. I think of sex constantly, a stranger's looking obviously up and down my body on the street makes me wet. I'm constantly aware of my pussy, sometimes lightly shifting in my chair to give it a teeny bit of friction. Sometimes fingering it to climax in a public restroom or while driving. The latter always done with an awareness that truckers might see in, which instead of causing discretion, leads me to deliberately slow into their line of sight, especially when a honk or light flash makes me aware they know, and like, what I'm doing.

So the thing I've found that is fun about posting ads is how pleasantly surprised the men are. First off they are surprised I'm real. I could be morbidly obese. I could have an ugly face. I could have a disfiguring scar; I could be dumb as fuck and they'd still be thrilled because I'm real, and because their expectations are low. In general these are men who are committed into sticking their cock into whatever they can find that is wet and willing.

The thing is I'm actually attractive, many would say very attractive. I'm older with a fetish for younger men. Cougar is an accurate term. I don't look my age though. I could easily pass for a decade younger than I am. I'm curvy (38DD) but not fat, and work out regularly. My skin is smooth and touchable. My hair is red. I'm well-groomed and generally well dressed; a professional. I come across as a little sexy without an obvious effort to be on a daily basis, and I'm willing to amp it up with heels, lingerie, and killer cleavage when the occasion warrants it. As you can tell, I'm also intelligent and can write. I'm sexually open-minded and comfortable explicitly sharing what I want in writing and in person. Put all together I'm frankly a walking wet dream for the average horny man whose into Craig's Lists lays. The first picture I send, always brings lots of praise and intensified interest, and I get a kinky thrill knowing they are beating off to images of my lips around their cock or pounding my pussy.

My ads always mention enjoying younger men. They also always mention smokers need not apply. I don't bother sharing a lot more because really the horny guys reply to everything. Old ones write (despite my requesting someone 25-35). Men write from hours away. It isn't about my sexy ad it's about playing the odds. They write to every woman, hoping for a real one, hoping for one that picks them. They really should the odds are stacked against them. Within 24 hours of posting I usually have more than 100 replies.

You would think that would mean that it would be easy to locate someone. Unfortunately that isn't at all the case. If you eliminate the ones far away, the ones who are too old or too young, the ones who are creepy, or sort of scary looking, about a tenth deserve follow up. From there scheduling difference lower that. There is also a group just looking for pen pals, skirting the edge of what they consider cheating with picture exchanges and cam sessions. Thus the most recent time I posted (the first in many years). I found myself still falling asleep frustrated and disappointed.

I had been talking to a guy who was interested in bringing his girlfriend along. From his picture he was attractive though looked a bit older than my ideal. She however was an adorable elven blonde, who I was more excited by of the pair. We had agreed to meet that night when she got home from work but that turned into too late to be practical.

It was extra disappointing because I not only had the house to myself for the weekend, but it was the last weekend I would for a while. The next day my sister was moving in with us to "get back on her feet". Privacy would be at a minimum for a while.

My disappointment turned to anticipation the next morning. The guy I'd talked to the night before offered to have a daytime tryst. His girlfriend was at work so it would just be the two of us, but he had mentioned multiple times his love of eating pussy and I really needed to get off. I cleaned up quickly, and tossed on a cute nightgown, knowing the royal purple looks good on me and the plunging cleavage emphasized my breasts and the hem that ended just below my ass would lead to speculation on what I had on under it.

His arrival was heralded by the dog going crazy in the way she does when strangers visit. I took a few moments to quiet her, knowing that my breasts were close to falling out as I leaned down. He kept saying, "wow! Wow!", as I stood and moved to give him a hug.

He was taller than I am and broader. Not skinny, not fat, not muscular, a good average body. His hair was shorter than in his picture. He had the look of a sales man, attractive, but not my typical type. I deliberately stayed close inside his personal space for a little longer than needed after the hug, keeping our body inches apart.

I invited him up to the extra bedroom, my sister would be moving into in a few hours, and told him I had a game for us to play. His hands grazed my body every chance he got as we went upstairs and got settled on the queen sized bed.

I pulled out a deck of cards and explained we were going to draw randomly. A club meant he could ask me a question; a spade that he could do something to me or have me do something to him for a minute; a diamond that I could ask him a question; a heart that I could do something to him or have him do something to me for a minute. As expected, he was up for it.

The first few draws went tamely. We learned about wildest places we'd had sex and favorite positions. I learned he had a bit of a foot fetish both from his answers and from the fact that one of his actions was taking a minute to kiss and suck my feet. My neck and cleavage got kissed too. I had him strip to his boxers at which point my suspicion he was hard was confirmed. I had oiled my legs before he arrived and I knew they were super soft even before it was obvious that he couldn't stop his hands from wandering over to stroke them as often as possible.

A ten of hearts came up and I instructed him to kiss and lick my thighs up to my nightie but didn't give him permission to move it. He kissed and nibbled as instructed and I felt myself getting wetter and wetter. With how close he was to my pussy he must have smelled my arousal.

The timer went off and he rolled away with a groan... "I want.. " he gasped leaving the rest unsaid. Up to that point he hadn't made it under my nightie but now I spread wide opening up my naked shaved pussy to him and entwined my hands in his hair. I pushed his face into me and told him to eat. The cards were knocked across the bed and the real game had begun.

The instant he started to work my pussy with his mouth, I knew it had been a good idea. The man had a talent, changing from lapping at my slit, to sucking my protruding lips, to massaging my clit, to shoving his tongue deep up inside me. Fingers joined in first one in my pussy, than two. I was moaning already and grinding into his face.

He shifted positions so his cock bobbed near my cheek and I turned my head to give it some attention. Starting with circles on the head, occasionally sucking just that in to my mouth and letting my tongue trace the slit. I moved down to lavish the same attention on his balls trying to retain my focus despite the waves of pleasure that his mouth and fingers were causing. I finally started to suck him in earnest from head down to where my lips touched his balls. The rhythm of his deep pussy licks matched that of his cock moving in and out of my hot wet mouth. We moved together faster and faster until at the brink of climax I had to stop, letting him fall out of my mouth and again grabbing his head and grinding into his face cumming all over it.

We fell apart breathing hard, his face shiny with my juices. I relished the taste as I kissed him deep on the mouth for the first time, letting our tongues tangle, his fingers still lightly stroking my wet slit, almost instantly re-exciting me. He pulls my nightie off at last freeing my breasts, and exposing my large hard nipples at last. He set about giving each tit attention with his hands and mouth before moving back to kiss me more.

The kisses deepened becoming frantic and our limbs tangled together and we continue to make out like teenagers for the next five minutes or so, naked bodies rubbing together. Finally his hands gripped my legs forcing them open as he positions himself above me. Moving his head against me, at first friction on the outside, not even lined up to enter me. I moaned and encouraged him, letting him know I wanted more, my fingers dug into his ass trying to force him to hurry and fuck me. His will power to resist was low and soon I felt his hard cock slamming into me. There was no need for gentleness. I was soaking wet and completely ready for deep hard penetration.

"Can I cum on you?" he asked. "Yes", was my frantic reply, but it doesn't happen before I do again and again. Finally I collapse a quivering puddle. I was worried he didn't enjoy it, but he explained that it is something he's used to. He can take hours to cum, which is why his girlfriend is open to him playing with others. She can't handle it-can't get him off- ever.

We laid together, sweaty, entwined, occasionally kissing, occasionally touching each other. Not quite sure if we were done. I suggest I could handle more with lube and pop out of the room to get some. Upon my return he took it and, opting to give my poor ravaged pussy a break squirted some between my breast, using his hands to spread it out so they are shiny and slippery. He mounted me, squeezing them together and started to slide in and out of them. I leaned over greedy to taste more and suck at his head and it thrust up to me. He told me he's never done this before. Moaning he, added me he had no idea how good it would feel. He's was moving faster and harder then, too fast for me to suck but my tongue remained out lapping as I was able.

He laid back and I straddled him. His hands were working my breast again, I leaned forward and he feasted on them. Licking and sucking with fervor. I knew, but don't care, that it is sure to leave them bruised. He slid back inside of me, the slight pain from overuse was completely overwhelmed by pleasure, and I moved up and down on him, noticing him enjoying the view of my heavy bouncing breasts. I continued to climax, unaware of the exact number of times I have at this point.

He roughly turned me over pulling me to my knees. I spread wide for him and felt him giving my pussy and ass a quick lick from behind in approval, before positioning his head against me and driving in once again. His hands were on my hips pull me back. I could both hear and feel the smack of his balls against my ass. With no warning he flipped me over and I felt hot cum starting to spray onto my tits. I opened my mouth and moved towards it hoping to catch and taste some. Sadly, I had acted too late, and had to content myself with cleaning him with light strokes of my tongue.

Again we found ourselves collapsed on the bed tangled together, sweaty, cum covered, exhausted. Still our hands and mouths kept finding each other lightly at first than starting to build up again. Fuck! We realized close to three hours had passed since his arrival. My sister was due anytime. I wouldn't even be able to wash the comforter. I was amused and appalled by that. Slower than was wise, with more kissing and touching we dressed and I walked him to the door- a final kiss, a final lift of my nightie hem and stroke of my swollen pussy, and he was gone.

My legs were still quivering as I cleaned up and changed into sweats to await my sister's arrival. When I was done, I went back to my email to scroll through what we said to each other earlier to find his name. I knew I was going to want to remember it.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
SilkessSilkessover 7 years ago
well written story

This turned me on... I gave it a 4 because I wanted a little more character development. There's something about a story that's just a sex act without getting enough about the person having the sex that detracts for me.

Still-- you have a ton of potential and are a very talented writer! Keep writing please

gunthernehmengunthernehmenalmost 8 years ago

@anon there's no romance because it's not about romance.

The story was effective. I liked it.

AnonymousAnonymousalmost 8 years ago

This is a very short story, mostly well-written, but it needs something to engage the reader.

"I deliberately stayed close inside his personal space for a little longer than needed after the hug"

Perfect opportunity to make us feel what she feels. Engage the senses. Can she feel the heat of his body, his breath on her cheek? What does he smell like? How does she feel - anxious. nervous, breathless, excited?

"My neck and cleavage got kissed too." How did his mouth feel on her? Hot, wet, eager, lingering?

"told him I had a game for us to play." What did she say? What did he say? She's invited a total stranger to her home to have sex with her and is totally blase about it all. It's like you wrote this in a big hurry and couldn't be bothered with those little details that would make it come to life. I would flesh it out, so to speak.

AnonymousAnonymousalmost 8 years ago

There's no conversation, no dialogue at all, besides, "Can I cum on you?" No indication of any emotions or thoughts about anything at all. They don't even have names! You keep switching from past to present tense.

Share this Story

Similar Stories

My Cougar Roommates A young man shacks up with older, more desperate, women.in Mature
Juliet Entertains Five Men Juliet ends up the stripper at her fiancé's stag party.in Loving Wives
Do You want to Fuck the Boss's Wife We had fun after finding the boss's wife at a pick-up bar.in Group Sex
Wife School Ch. 01 Everyone wants a better wife. Some people get them.in Loving Wives
Carla, "The Hot Wife" I am loving being shared with my husband's best friend's.in Erotic Couplings
More Stories