age difference

Jill stood outside her car for a moment before walking into the banquet hall. In less than a month, she had experienced so much… all because of this stupid bachelorette party.

She wasn’t sure why she hadn’t worn her contact lenses. She knew she needed her glasses to drive, so rather than lose them; she left her glasses in the car, just to be safe.

Jill had given her sack full of party favors to Tammy, the maid-of-honor, and Tammy wrote Jill a check for the full amount.

“What’s this?” Jill asked, looking at the check.

“We didn’t expect you to spend a thousand dollars of your own money on a sack full of dildos and vibrators, Miss Jill.” Tammy smiled. “You just had to do the dirty work of getting them. I’m impressed. You found every one on the list! I hope it wasn’t too much trouble.”

“It wasn’t what I expected, I can tell you that.” Jill answered.

Tammy knew exactly what Jill meant. She had seen the video of Jill be fucked in every possible position by a half-dozen men. Some of those men would be at the party performing as strippers, and she wondered if Jill was going to let loose and provide an encore.

The women attending ranged in age from 18 to 68 years old. Jill took comfort in knowing that the dildos were kept secret, as not everyone was going to get one. Instead, most of the evening was spent with the forty women in attendance sharing stories with the bride-to-be on every topic revolving around a good marriage. The food was excellent. The dessert was classy. The drinks were free. Jill wondered how in the world a 20 year-old could afford to throw a party, as the bride-to-be insisted on paying for everything herself.

After about three hours, Tammy and some of the banquet hall staff carted in a few serving tables with party favor and gift bags. None of them were big enough to conceal some of the toys she had acquired. Jill peaked inside one of the bags and found condoms, male porn magazines, lubricant, and coupons to an upscale day spa.

A few of the women seemed to know there was more planned for the evening, but didn’t say anything. Most of the older women and a few of the younger ones took the opportunity to take their gifts, say their goodbyes, and make it an early night.

The rest of the women, including Jill, took seats close to the dance floor.

The banquet hall staff cleared off the tables, but kept the bar open. Jill looked around and counted just over a dozen women remaining, including Andi and the other bridesmaids.

Tammy had the staff dim the lights and turn on a disco ball over the dance floor.

“Okay, ladies. We all know that if the guys can have girls at their bachelor parties, they’ll want them to be strippers.” Tammy said as she walked to the center of the dance floor. “Some guys will want them to do more than strip, and I think that’s okay — as long as they don’t mind if we want the same.”

The bride-to-be stood up and next to her maid-of-honor. “I want you to have fun tonight. But whatever you see here, stays with you. Okay?” All of the women nodded, not knowing exactly what she meant. Jill knew they were about to find out when Tammy held up a green wristband.

“If you see a green wristband, the guy is recently-tested and disease-free.” Tammy said sternly. “If you don’t see one of these, lick, suck, and fuck at your own risk.”

“Oh, and one more thing,” Tammy added. “Put these on and leave them on until you step out of the building.” Tammy held up a mask similar to those worn at Mardi Gras. On one of the tables behind Jill, there was a pile of more masks, each varying slightly from the other, but whose purpose was identical: a very feeble attempt at anonymity.

Tammy dragged a chair to the center of the dance floor, cueing the banquet hall staff to start the music. The bride-to-be quickly took her seat as the first three male strippers strutted onto the dance floor. She put on her mask and jokingly licked her lips while rubbing her breasts and pussy through her blouse and skirt.

The music was loud, but not deafening. The strippers weren’t much for dancing, as they mainly strutted in time with the music and allowed their groins to sway in an exaggerated manner. They also wore masks, which covered their foreheads, eyes, nose, but left their chins and most of their mouths exposed. The G-strings they wore left nothing to the imagination, barely covering half the length of their half-erect cocks. All three of the men had shaved their chest and pubic hair, and lathered their bodies with suntan lotion or baby oil. The obligatory bow tie and cuff links completed the ensemble.

Tammy grabbed a microphone. “We all know the bride-to-be worked in the film industry.” Two of the strippers took hold of either side of the chair and carefully lifted the chair and turned the bride-to-be so her back was to the other women. The strippers stepped away from the chair and closer to the women in the audience. As they gyrated their hips, one of the strippers allowed his cock to come unsheathed. He made no effort to tuck it back into its hammock.

Jill couldn’t be sure without her glasses, but the stripper with the free-hanging dick looked like Wayne, one of Andi and Mark’s friends. The other strippers then stepped out of their G-strings, exposing thick, half-erect examples of the male anatomy.

“I’ve always wondered what it’d be like to be fucked by a dick that big,” Mrs. Paladino whispered to Jill. Jill was taken by surprise at the 55 year-old woman’s comment.

“Our bride-to-be would like to thank you all for your advice on how to pleasure a man,” Tammy continued. “But I think you’ll see, she’s already a pro in that area.”

The three strippers stood in front of the bride-to-be, shoulder-to-shoulder. The women in the audience watched as she leaned forward and took the first stripper’s cock in her mouth. She sucked hard, then let it pop out of her mouth so she could lick the shaft, then his balls, and then took half his length down her throat. He became instantly erect and stepped aside.

She took the next stripper’s cock in her mouth and eased his full length down her throat and kept it there for a few seconds. As she backed away, she reached up and massaged his balls, and then took his length down her throat again. Within seconds, the stripper’s tool was pointing toward the ceiling.

The third stripper’s cock was much thicker than the previous two. The bride-to-be could barely get her mouth over the head of his flaccid member. She used both hands to stroke him rather roughly, then pulled his thickening tool from her mouth and rubbed its saliva-covered head on her lips, nose, and forehead. The dick seemed to double in girth almost immediately.

“Ladies, our bride-to-be is a recently retired fluff girl.” Tammy said, unbuttoning her blouse. “She’s probably sucked more dicks than all of you put together. But she’s never been allowed to take them all the way to orgasm — until tonight!”

Tammy stepped off the dance floor, picked up a long box, and then stepped back under the disco ball. “Don’t worry. She doesn’t get to have all the fun. If any of you can suck a dick as good as her — or can make our strippers come in any other way — you can win one of these little numbers.” Tammy pulled one of the large dildos from its box. Mrs. Paladino leaned towards Jill. “I want one of those.”

“Ladies, allow me to bring out the rest of the entertainment. Have a good time!” Tammy guided a half-dozen more men in line in front of the bride-to-be. One-by-one, she brought them to erection. The first three strippers walked up to the three closest women and swayed their erect cocks inches from their faces. Two of the women just smiled toward each other and laughed, but the 18 year-old reached out and pulled one of the strippers by his dick toward her. The stripper grimaced in pain as the inexperienced girl dug into his foreskin with her teeth. He withdrew his cock from her mouth, smiling uncomfortably, and stepped aside to another girl.

Jill knew the next girl was her daughter, Andi.

Andi took half the stripper’s length down her throat before bobbing her head up and down, and tilting her head left and right with each bob.

“Oh my god, Andi.” Jill said under her breath.

The stripper opened his mouth as his legs began to shake. He held his hands on his hips, ensuring that whatever this girl was doing was completely voluntary. Andi engulfed two-thirds of his long tool down her throat and locked her lips around his shaft. He came quickly. The stripper waived at Tammy.

“It appears we have our first winner!” Tammy exclaimed. “Pick your prize, sweetheart.”

Andi chose one of the biggest dildos in the collection. “Congratulations. Nice choice.” Tammy added. “Want another one?”

Each of the strippers took a few moments to dance in front of each of the women. If the women were interested in becoming part of the show, all they had to do is lean forward and take a cock in their mouths. If they didn’t want to participate, the stripper politely shook their hand and stepped to the next woman.

Andi let a few more of the strippers go by, but stopped a particularly large black man. He was big in every respect, and was endowed with the largest dick Jill had ever seen. Jill suddenly realized she had seen that black monster before. Andi was blowing Dee.

As good as she was at sucking dick, Andi could not seem to make Dee come. He leaned forward and said something in Andi’s ear, and then stepped aside to the next woman.

Jill looked at the next few men in line. She immediately recognized Andi’s boyfriend, Mark among them. She was so absorbed in watching Andi blow Dee and now Mark, she barely noticed Mrs. Paladino on her back on the table behind her. Wayne had a calf in each hand as he buried his fat dick in her 55 year-old hairless pussy.

Wayne called over to Jill. “What do you say, Red? You want to go next?”

“No thanks.” Jill smiled politely. Her pussy was uncontrollably wet. She knew she had soaked her panties.

Jill stood up and quickly walked to the restroom.

She looked in the mirror and removed her mask, the outline of the mask remaining on her face. She entered a stall, sat and peed. She peeled off her panties, patted her pussy dry, and then stepped out to find Mark waiting for her.

“Getting ready?” Mark asked, eyeing the wadded panties in her hand.

“Go away, Mark.” Jill answered, dropping the panties in the trash.

“I know you want it, Red.” Mark said, as he stepped closer. His large dick bounced before her.

She turned as if ignoring him. She pretended to wash her hands and then placed her mask on her face. She leaned closer to the mirror to check for lipstick on her teeth, cursing herself for not having worn her contact lenses.

Suddenly, Mark was behind her. He put an arm around her waist and a hand around her throat, squeezing both firmly.

“You’re not going to let Andi win all the dildos, are you?” He said as he quickly turned her around to face him.

Mark lifted Jill’s ass and sat her on the restroom vanity. She was afraid, but she was also unwillingly turned on. He easily entered her wet pussy. She remembered how good he was at fucking, and pulled his head closer to kiss him. Jill’s toes curled in her high-heeled sandals as Mark brought her to the brink of orgasm.

Mark felt her pussy tighten around his shaft and quickly withdrew his swollen cock.

“Oh no you don’t, Red.” Mark warned. “You’re supposed to make ME come.”

Jill pleaded with him to finish, that she was so close, but Mark didn’t listen. He pulled her off the vanity and turned her around so they both faced the mirror. She knew what was coming, next.

Jill arched her back as Mark twisted the head of his dick and pushed it against the bud of her anus. She exhaled as he eased in the first two inches.

“Yeah, you stretched it out a little, slut.” Mark held her hips firmly. “But you’re still a hell of a lot tighter than Andi.”

Jill pushed back hard against Mark, and the pain almost caused her to pass out.

“You’re gonna tear yourself up if you keep doing that.” Mark feigned concern.

Jill pushed him back, caused her asshole to pop as his dick exited.

She turned around and squatted, intending to spit on his dick, and then on her hand so she could lubricate her asshole, but Mark had other ideas.

“That’s a good idea. Suck my dick for a while. Taste your ass.” Mark pushed the head of his cock past her lips.

Jill protested, but not for long. She sucked him to full erection, and coated his tool with as much saliva as she could produce. As she stood up, Mark pushed her forward and spread her legs. Jill arched her back further, angling her anus upward, allowing it to open slightly. Mark spit into her asshole just before sliding half his length inside her.

“Isn’t that better, Red?” Mark asked.

Jill moaned and pushed back, causing her to fart around his shaft. She wasn’t embarrassed. She was well past that.

Mark expertly fucked her ass for several minutes. Every time Jill reached down to rub her clit, Mark would grab her hand and place it back on the vanity.

As Mark’s thrusts became more painful, he graciously stopped and allowed Jill to blow him, lathering his cock with her spit before putting it back in her ass. Each time, he was able to ease in a little more of his dick, until his entire length was inside her.

Jill’s legs shook. She knew Mark was going to be angry, but she couldn’t help it. He was actually going to make her come by fucking her in the ass. Her eyes were tightly shut as Andi walked into the restroom. Mark looked at Andi in the mirror, winked, and slapped Andi’s mother’s ass.

Jill opened her eyes just as Andi ran out of the restroom.

“You son of a bitch!” Jill said as Mark filled her rectum with come.

Mark smiled and laughed to himself as he washed his dick in the sink next to Jill.

Jill stood, come dripping down her leg, sweaty and exhausted.

“Come on, let’s go. Time to get a prize.” Mark grabbed Jill by the arm and led her back to the banquet room.

Jill suddenly realized she must have been in the restroom for quite some time, as the number of strippers now outnumbered the number of women. Several of the women were straddling strippers, cocks buried in their pussies. The bride-to-be had several loads of come deposited on her blouse and skirt. Tammy was walking around topless.

Andi had several dildos on the table next to her, and a line forming in front of her and one behind her.

The well-lit restroom was a stark contrast to the dimly lit banquet hall, and Jill had trouble walking toward the dance floor without bumping into something.

Tammy leaned toward Mark, telling him the try-outs were complete. He leaned back and said we had another winner, pointing in Jill’s direction and eyeing the come dripping down the inside of her thigh.

“Sorry, Jill, I think Andi won all the dildos we had left. Who knew?” Tammy smiled as she bent down to suck Mark’s dick.

Jill watched as several men filled Andi’s mouth and ass with come, sometimes simultaneously. She stared as the third stripper in line for Andi’s mouth looked unlike the others. Maybe older? Something looked familiar about him. She tried to get closer as he went from third position to second.

Jill still couldn’t make out whom it was, as he had his back to her and was wearing a mask, tie and cufflinks like the other strippers.

She worked her way closer until she was alongside Andi — who was obviously very drunk or high. She would talk to her about that, later.

As the older, familiar-looking stripper took his place at her daughter’s mouth, Jill froze.

There was no mistaking her husband’s cock, even without her glasses.

Chapter 1

Warm up and stretch.

At 7.30 in the morning it was already too hot and I was finding it difficult not to fidget as sweat trickling down my back pooling between my butt cheeks and soaking into the top of my electric blue running shorts.

I had recently started to run the trail path of NYC’s Van Courtland Park with my friend Jessie. An older Dominican woman I knew through my Aunt, Titi Santina.

Jessie was a little late and my mind was starting to wander. I imagined what I must look like to the other people in the park. They would see a short Puerto Rican girl with long curly hair tied back, framing a soft, sensual face with large dark eyes and plumb kissy lips. My skin is very lightly freckled and a rich golden olive tan. Legs, toned; the sculpted curves of an enthusiastic runner. My legs bumped the high, round and generous cheeks of my ass which curved together with my stomach and though tight, stuck out and was a endless source of fuel for Jessie to tease me. Calling me all sorts of names that referred to my proud proportions. The most common was Beany because years ago she noticed that in profile my body had the shape of a kidney bean. And when I thought of how I looked I would also think of how good Jessie and me must have looked together. If I was the kitten she was the cat. Her feline, mischievous mouth clashed with intense green eyes that almost glowed, framed by large, arched eyebrows. Skin a warm tone between caramel and chestnut. Jessie’s strong thick curves were somewhat similar to mine apart from one obvious difference. Her large pendulous breasts.

As I waited I floated into fantasy. Vague images. Scenes of catching Jessie changing. Glimpsing her tits free and on display, maybe a peek of her pussy as we undress for a swim…

Catching myself I focused on the moment, back to reality.

I bounced on the balls of my feet. Squinting, watching the low sun flicker through the trees. I concentrated on my breathing. My cute 32B breasts snug under the tshirt that already had a small batch of sweat soaking through at the collar.

With a yelp I caught the sting of a slap on my butt and suddenly Jessie was running in front of me. She spun around and with a flick of her tongue and with a low giggle said,

” Keep up Champ we got 3 miles of trail to work through.”

I felt my stomach in my month. Jessie looked amazing. Her tight white running shirt left her arms bare and her bust and belly covered but still so plumb and full. As usual her shorts where too short and so hot. Her phone in an interior pocket, making a small angular lump on her right hip. As her round, full cheeks bounced the bottom of her sheer, black shorts would flick up and I would get a flash of the base of her ass cheeks. That little wrinkle where cheek meets thigh getting tight then loose, tight then loose. I quickly caught up to her and we started our usual routine of work gossip and chat about various TV shows. I stole glances at my magnificent running partner. Watched sweat patches grow. The bounce of her juicy curves, her thick dark curly hair pulled back into a flowing ponytail. Even though I was focused on the run I felt a vague flicker in my pussy. My kitten had started to purr.

As we climbed the hill our chat slowed. Sweat streamed down our faces. We must have been about a mile into the run when Jessie took a detour off the path.

“Beany in gotta pee,” she squeaked as I watched her sweaty curves disappears into the woods. I spun on my heels and was quickly right behind her as we followed a vague path deep into the thick foliage. After about 15 seconds Jessie led me into a small clearing.

She hooked her thumbs around her waistband and asked if we were alone.

” Of course,” I said. “We’re in the middle of nowhere.”

With a face of desperation and gulping air Jessie muttered “Good, Just you and me.”

My head darted about looking for anybody that may stumble past us. Jessie’s shorts and panties were so drenched in sweat that she having trouble peeling them past her generously sized rear end. She looked over her shoulder at me with a mixture of comedic horror and frustration, ” I really gotta pee!” she hissed. She sucked her teeth, realized her phone was getting in the way and passed it to me. So at last at the top of her butt crack appeared and she tugged the kit past her tush. Perhaps she heard me gasp as I had my first good look at her bare behind. Though her skin was a warm brown her tan lines were still quite visible and incredibly sexy. My stomach tightened as a warm tingle tickled my sex.

With her shorts and panties around her ankles she looked around and asked for confirmation that no one was coming. I had no idea. Her butt had hypnotized me and my pee watchman job had totally slipped my mind. With a half assed, “You’re fine.” from me she squatted, looking over her shoulder again at me, paused then a tiny squirt of pee escaped. The sound of the piss on the forest floor and the sparkle of light that refracted off the tiny gush forced my attention to Jessie’s spread butt as she squatted. What startled me was the hairyness. I expected a trim bush like mine but no, Jessie’s muff was furry and pitch black with thick pubes. With the light behind her she was almost silhouetted so I couldn’t see much detail but my attention was snapped away from her rear by her low moan. The squirt of piss from a second ago was followed by a pressure hose of crystal clear pee. It hit the ground, splashing the inside of Jessie’s ankles and wetting her spread cheeks and the back of her running shorts, which she was now desperately tugging forward. Still peeing with the force of a thoroughbred Jessie looked back over her shoulder at me and mumbled, “Now that’s good.” but seeing I was staring at her soaking peach she snapped the clichéd, “Take a picture, it’ll last longer.” Caught, I gave a guilty grin, felt my eyebrows raise two foot and realized I was vaguely stroking my clit through my shorts. I laughed, Jessie giggled then my mind sprung into perverted action. Reaching behind me I grabbed Jessie phone. As she stumbled up straight, grappling

with her sodden shorts I snapped a photo her. “You dirty bitch! You got me.” Jessie yelped. Then firing blind I snapped another photo of her. Jessie was stunned, prone as kitten with her wet kit still halfway up her thighs. Her big round butt glistening with sweat and a splash of pee.

With the most evil of grins she pulled her kit back down and teased me with, “Hey Mami, I’ll give you something to remember me by.” One foot quickly stepped out of her shorts, her shoulders lowered, she reached behind to the inside of her cheeks and with what seemed like no effort she spread her ass. Raising her phone I snapped off a photo with out looking. My stomach flipping and even with my sweaty crotch my wet pussy was becoming overwhelming.

The moment was so uncomfortable. I was lost with no idea what to do next then out of the corner of my eye I noticed two other runners just cresting the ridge. Tapping Jessie’s arm I pointed at them and with out a word she quickly tugged her shorts back up and I slipped her phone into the tight pocket of my shorts. We trotted back to the main path. Joining about 20 yards behind the two other runners. For about 5 minutes we ran in silence. I desperately wanted to say something but I had no idea what. Leaving the dirt track we hit the tarmac road that went past the old, dilapidated Park Ranger’s hut. The unspoken tension was broken when Jessie pulling up. A stone in her shoe had nipped her heel and hobbling to the hut she leant again the wall and pulled off her sneaker. Shaking the pebble out she asked how the photos looked. Her direct question came as somewhat of a relief and I answered her honestly that I didn’t even get a chance to check them out. Her damp tush was distraction enough. Asking for the phone she said it was best that they were deleted. Reluctantly I agree, wishing I had at least got a glimpse of then. As I handed the phone to Jessie our fingers brushed and eyes met. Again Jessie flashed that wicked smile, “This is exciting yes?”.

“Yes, well exercise gets the endorphins pumping. The blood busy.” I answered. Desperately trying to suppress a childish giggle.

“So, these photo’s you took of me. How slutty do I look?”

“To be honest Jessie you look slutty in every photo, so these, if I had to guess will be off the charts!”

“We’ll see.” then opening up her gallery she laughed and turned the camera for me to see.

The first photo was pure comedy. Her butt was not even in the shot and her head in three quarter profile, low in frame with a goofy mask of relief. A woman peeing who had been holding it in for a while. More forest glade than smut.

Brushing off the photo with hands on my hips I confidently stated, “See, you’ve nothing to worry about.”

“Uh huh, Beany.” Looking deep into me then back at her gallery she swipped to the next photo, “So it looks like you’re an artist.” Looking at the photo I saw what she meant. The low morning sun was right behind her and only Jessie’s back from shoulders to knees were visible. The squat had spread her cheeks with the forest of pubes and meaty pussy lips black, silhouetted and partially hidden by lens flare. Light danced off the puddle beneath her and the drops attached to her bush. I felt a mixture of disappointment and confusion when I realized that the silhouetted nature of the photo had hidden any detail of her butt hole. Why on earth was I so desperate to check out Jessie’s ass? Then of course, like some Santeria Priestess, Jessie read my mind, “Lucky you didn’t catch my asshole. I’d so embarrassed.”

“Well it looks like you’re all good. These are nothing. Rude fun.”

“But the last one Beany. I know you haven’t forgot you took it.”

“It’ll be of a tree and your shoulder.”

Jessie looked at her phone then at me with genuine shock.

“It’s a little more than that B.” and Jessie passed me then phone.

I made a low, slight squeal. The picture was pure filth. Jessie looking over her shoulder straight at the viewer. Her face almost snarling, daring you to challenge her. Sweat plastering hair to forehead. Brow furrowed in some kind of sensual fever. Her running tanktop drenched in sweat, riding up her back with the thick straps of her sports bra exposed. Her hands clamp around her cheeks and with such a fierce thrill I see her left fingers are only an inch or so away from her hairy asshole. Distorting, pulling and slightly opening it. Winking the bright pink eye. The right hand is lower on the right butt cheek and nearer Jessie’s pussy, tugging it slightly open. Through her thick black pubes, between her milk chocolate lips the sopping wet pink of her sex leaps out. Jessie stepped beside me so we could both look at the photo at the same time. Her sweaty shoulder brushed me and was almost eye level with her fat, massive titties.

” I can zoom in.” she whispered and pinching the screen with her fingers we both got a close up of her drenched pussy and ass. Pubes held droplets of moister. The wrinkled texture of her distorted anus and labia seemed so perfect and contrasted with the pink shiny inner folds of her sex.

Jessie muttered, “If I could eat me I would.”

I gulped and resided the urge to make eye contact with her but I couldn’t and she leaned forward…and pulled her running shoe back on. I stood there with my knees shaking and a puddle of juice in my running shorts as Jessie ran on, back toward the trail.

I got my shit together and desperately tried to forget the previous 10 minutes. After another half hour of running and distracted small talk we arrived at our starting place. Both sweating heavenly and buzzing from the strange bit of lesbian play we did our usual breakdown of our run. As we discussed our pace and the condition of the path it became obvious that neither of us was going to mention the photos. That was fine by me because I was still trying to process what had happened. So the uncomfortable conversation trailed off and Jessie hugged me goodbye. We separated with our usual hug and mumbled an agreement to meet same time tomorrow. I watched her walk back toward the car park. Her dark Dominican skin glistening and large round butt bouncing with each step.


Chapter 2

The cautious jog.

As the rest of the day went on I constantly fought the urge to cancel the next days run but my conflicted feelings about the mornings events kept being suppressed by one dominant feeling, I enjoyed it all so much.

I left work totally spaced out, Jessies curves dominated every thought and as my train rumbled up to Yonkers I had to almost wrestle my hand away from strolling inside my panties. I had never felt so horny.

Before the days Sapphic fun run I had played around with a couple of girls. The first was my cousin’s fat Jamaican bridesmaid who ate my pussy during the drunken hen weekend in Cancun. After I had almost died due to the amazing orgasm she’d forced on me she just raised my legs up, kissed my asshole then walked back down to the hotel bar. I was relieved I wasn’t expected to eat her out because the idea of returning the favor freaked me out.

Then a Skype cam chat with my old boss (a skinny red headed Irish woman) once ended up me naked and fingering my spread pussy after she watched urging me on with filthy commentary and her right hand busy between her legs beneath the camera’s gaze.

I spent plenty of time with both woman after the encounters but the lesbian shenanigans where never mentioned which was fine by me.

There are few things that smoother my libido but my parents badgering me is one of them and the moment I got home they were on my case. I had moved back home 4 months earlier, after my asshole ex-fiancé was arrested, naked and smoking crack with his withered Bitch of an ex. Bombarded with questions, suggestions and ideas about getting my life back on track I dodged their interference, grabbed my laptop and flopped onto the couch with my earphones in and a bowl of my Moms Chicken and rice. Just as I was about to crank Muse up I heard something that almost made my spit-take my soda. My Mom had met Jessie at the supermarket and Jessie was so grateful I was helping her get back into shape. Struggling to keep composed and just gave my puppy dog eyes and whined, “Mom I’m really tired.” And so with a warm empathetic smile Mom went back to the kitchen to bother my Dad about whatever harebrained business scheme he was brewing up.

Facebook was dead. Just the usual mixture of bitchiness and reminders that I had so little. I checked out a couple of Stephenie Meyer’s forums but found no friends on the chatrooms so after wasting more time on hoping to raise a smile I felt lost. An incredibly confusing day had crashed around me and I felt empty. Then as force of habit and without thinking about it I decided I might as well check my email. Something I rarely did.

Who emails me expect spammers and my weird cousin Charles in New Orleans.

Who emails me? Jessie emails me. My stomach flipped again and the universe held it’s breath. The email was titled “Track maps” and 6 jpegs were attached. Of course I scrolled down immediately but to my immense disappoint found exactly that. Maps of other trail running routes in New York. Until then I had not admitted to myself how desperately I wanted to see those photos again. And to be honest why would Jessie risk giving me copies of such sleazy photos of her? She played an active and influential part in our local Spanish speaking community. My hand dropped away from the laptop’s touchpad and I felt the early budding of tears. Pathetic. Then the smallest spark got my attention through the bleak fog. There were 6 jpegs attached. I had just scrapped the top of the third then surrendered when I saw it was another fucking map. The other three jpegs were..?

Yes, the fourth was the goofy profile of Jessie’s head, the fifth her shoulders to knees silhouetted and the sixth? I paused did she really send that one. Really?

She did.

I stared at it. Stunned emotions bounced around inside me. Agony and ecstasy.

Jessie’s face distorted with lust in the photo. Her sex displayed to me like a prize. My prize.

Then beneath it was the clearest message I could of hoped for, ” I trust you Beany.”

I saved the photos to a hidden file then deleted the email.

My pussy now ached for attention. Flexing and grinding inner thighs together I caught myself grinning like some dumb stoner. I needed to be alone and so mumbling some vague explanation to my parents I headed to my room with my laptop and wet panties.

Almost tripping up as I rushed into my room I shut my blinds, opened my laptop and clicked the file. The little thumbnails teased me. Small reminders, vague shapes, contrasting colors in miniature. I started to undress down to my bra and panties. Clothes scattered around my bedroom. Then as I watched intensely in my full length mirror I reached behind me and started to unclasp my bra. Admiring my fine Latina curves, suddenly very conscious of my breathing, I focused on my wet panties, transparent with my juice and clinging to the valley and ridge of my pussy. A camel toe smiling at me.

Thinking of the sensation coming up. An orgasm with Jessie. Her hairy pussy and big round chestnut butt calling me in digital clarity.

Biting my bottom lip, my titties almost free…

Then suddenly there’s a commotion downstairs, my father yelled. Something smashed.

Instinctively I shut my laptop, pulled on my gown and paused to catch my breath. The ruckus down stairs continued. My name called. The harsh thud of a slammed door resonated through the walls and then I knew what was up. My parents had drunk a beer too many and rows from weeks, months, years ago and burst back into life. Evening over. Pussy play turned to dust.

And so thirty seconds later my Mum in tears and at my bedroom door, asking if she could spent the night in my room on what had long ago been christened the Booze battle cot.

I fell asleep to the all too familiar sound of my Mom’s low grumble of complaint. My Father this, my Father that. My damp panties rubbing against my inner thighs. Under the covers a finger very gently flicking my clit. Flexing my asshole and tickling it with my left pinky finger.


Chapter 3

The sprint never ends.

My dreams were a jumble of images, hardly remembered but defiantly sordid and interrupted by the shrill, electronic squawk of an early morning text. Jessie’s message was brief but clear ‘I hope you’re ready.” Without hesitating I texted back through drowsy, squinting eyes, “20 minutes. We’ll have fun.”. Stopping to take a whiff of my fingers. Rich and thick with the strong musky smell of my pussy. My hand strayed back down South but with a feat of superhuman strength I resisted and hopped out of bed, skipped over my snoring Mother and darted into the bathroom. A pee, a 5 minute shower and a big glass of cold water later I was naked, back in my bedroom and choosing something to wear. There was one outfit that screamed at me and with a muffled giggle I slipped into it. Kissing my sleeping Mother goodbye I left home and jogged lightly to the Park. The air smelled fresh and looked so clear. A low morning sun picked out the pin pricks of dew on the grass and I had never felt more alive. My titties, sensitive and almost heaving. A new sensation to me considering their petit, tight size. As I rounded the corner of my block and the Van Courtland park came into view my sex almost inhaled. My clit gave a vague twitch and my tiny taint seemed to tighten. Suddenly my plump bottom lip were stinging because I was biting it so hard. Now at our meeting spot I had a pinch of panic. Where was Jessie? Looking toward the car park I couldn’t see her. Was she blowing me out? A humiliating trick? Rev me up the leave me to bounce around with a unscratchable itch. I couldn’t see Jessie. Nothing between me and car park expect a fat herb walking a tiny dog.

Andi appreciated the fact that her aunt never gave her a hard time about saying “exactly” where she was going, as long as her aunt knew how to reach her. Andi could stay out all night most weekends, checking in several times during the night to let her aunt know she was okay.

She pulled her skirt up, zipped the hidden side zipper on the waistline, and adjusted the belt. Tommy had licked her to orgasm for the third time this afternoon, and his jaw was tired. Andi liked Tommy because he was happy with a simple blowjob, and wouldn’t turn one down, no matter where Andi wanted to blow him.

She had decided to go out without a bra or panties and the feeling was exhilarating. Her breasts didn’t require the support of a bra just yet. The fabric of her tiny sport shirt slid across her nipples as she moved, constantly reminding her of her naughtiness. It seemed to leave her groomed pussy perpetually wet.

Andi had experimented with thong underwear, and found they weren’t very functional. Soft cotton panties were a must for her period, but the rest of the time, she decided she would just go “commando.” She liked the open-air feeling, especially while wearing a denim skirt.

She thought again about her promise to her mom.

Jill sat with her on the eve of her 18th birthday and pleaded with her to do her best to remain a virgin until she was married. Jill gave her permission to do anything else with boys, knowing she would probably be asked to blow whatever boyfriends came along. She didn’t know Andi would exploit the loophole in her promise, and engage in anal sex. In Andi’s mind, whether in her mouth or in her butt, she was just making the guy feel good enough to stick around.

Her reward was a boy’s mouth on her clitoris. While she wondered what it would be like to have a thick cock shoved deep inside her pussy, she was happy knowing she could have an orgasm without having to worry about accidentally becoming pregnant.

Jill liked Tommy as a “friend with benefits,” but she really had a thing for Mark. She wished that he didn’t have so many other girlfriends. If he were only able to keep it in his pants, Mark would be marrying material. He came from a wealthy family, he was handsome, and he was very well endowed. He just liked to fuck a little too much to stay with just one girl.

He had dated Andi for a few months without seeing other girls, but when their relationship bordered on becoming sexual after her 18th birthday, Andi told him about her promise to her mom. Mark became frustrated and soon cheated on her — a lot.

Andi, in turn, decided to get even, and propositioned Mark’s friend, Wayne. Wayne was a very big boy. He was also in possession of a very fat dick. Andi had handled a few penises before, but wondered when they got older if they were all as big as Wayne’s. She had absolutely no idea how to perform oral sex on a guy, but Wayne was patient. He taught her the basics, and as best she could, she learned to suck and swallow.

It was Wayne’s idea to suggest Andi try anal sex in an effort to win Mark back. He even introduced Andi to a few other friends that were much less endowed, so she could experiment.

Every boy that Wayne introduced to Andi was kind and gentle. Andi became very good at oral sex, both giving and receiving. The boys all understood that her pussy was off limits for fucking, but her ass was ready and willing.

Eventually, Andi became so accustomed to anal sex that she wanted to let Wayne try stuffing his fat dick up her ass.

At first, it hurt as much as it did the first time someone shoved a dry finger in her ass. But after several tries over several occasions, she could take half Wayne’s length and his full girth.

Mark’s cock wasn’t quite as fat, but it was still big, and a little longer. She knew that he had probably fucked at least a dozen other girls from the time they had first dated. She suspected that Mark knew that she had just as many guys in her mouth and in her ass during the same amount of time. Mark and Wayne were still good friends.

None of the other girls Mark had been with were really into oral or anal sex, so the thought of fucking Andi in the ass — and her liking it — intrigued him.

Over the past few weekends, Mark fucked Andi’s mouth and ass a dozen times, and she kept coming back for more.

Andi adjusted her denim skirt as she walked into the hardware store where Mark worked part-time.

“You’re early,” Mark said from behind the counter. “I don’t get off for another hour.”

“Really?” Andi asked. “I thought you might want to get off sooner.” She turned around and bent over at the waist, allowing a clear view of her firm ass and thighs.

She pretended to be looking at something on a lower shelf, but stood up abruptly as an old man with a plunger walked by. Andi smiled shyly, and then proceeded to walk around the store, flashing her bare ass in Mark’s direction as he handed the customer a receipt.

Mark was quick to follow the customer to the door. As the old man left the store, Mark locked the door and placed the “Be back in 15 minutes” sign in the window. He turned around and Andi was nowhere in sight.

After walking up and down the isles, Mark looked inside the break room. There, Andi had stripped completely naked, not that what she was wearing earlier left much to the imagination. She was lying on the table, legs spread, and two fingers already in her asshole. With the grace of a gymnast, she hopped off the table and unzipped Mark’s pants. Within seconds, she had half his shaft down her throat.

Before he could object, she stood and turned facing away from him. She guided his cock to her pussy, rubbing the swollen head between her labia.

Mark pushed his cock into her pussy, but she quickly jumped forward enough to avoid penetration. She reached behind her and guided his thick tool to her anus, pushing herself backward onto him. With a “pop” he was inside her.

“Andi, you really need to wait until I’m off work for this,” Mark feigned protest.

Andi pushed back harder until half his shaft was in her ass. Her pussy was dripping wet as she rubbed her clit and squeezed her tits while bucking backward against him.

Suddenly, an old man stumbled into the room. It was the storeowner, Mr. Genge.

“What the hell is going on in here?” Mr. Genge yelled.

Mark and Andi ignored him as Andi quickened her pace. Mark had sat on a steel folding chair, and it squeaked with every impalement Andi gave to her asshole. Mark let Andi do all the work, as she knew exactly what she was doing.

“Young lady, I’m inclined to tell your mother about this. Now, stop this instant!” Mr. Genge said firmly. Andi could see the bulge forming in his trousers.

“Mr. Genge, pull that old dick of yours out. I’ll suck you off if you forget this ever happened.” Andi alternated between smiles and moans.

The old man was frozen. He wasn’t sure what to do. He never thought he would ever have his dick sucked again after his wife died years earlier. He knew Andi. He knew she was old enough. He also couldn’t help but notice his employee was stuffing her ass with a dick twice the size of his. He quickly fumbled with his belt and zipper and waddled in front of Andi.

“That’s it, pull it out for me.” Andi leaned forward.

Mark stood up behind her and grabbed her hips. He was in control now, sinking the full length of his cock inside her. He watched as Andi took Mr. Genges cock in her mouth and down her throat. For an old man, he was respectably endowed and rigid.

Mark fucked Andi’s ass harder and deeper than he had done before. She didn’t complain or cry out in pain. He thought to himself, “whoring must run in the family” but that wasn’t necessarily a bad thing. She wasn’t “wife material” but she was definitely worth keeping around for a quality blowjob or ass fuck. Her mother may have had a tighter ass, but Andi put on a better show. He couldn’t help but look at Andi’s back, shoulders, and hips and be reminded of Jill’s similar frame.

Within minutes, Mr. Genge was filling Andi’s mouth with come, which she quickly swallowed. She knew the longer she kept his come in her mouth, the more likely she would be to throw up. Best to get it down quickly.

Just as quickly, she felt Mark’s cock spasm inside her, followed by a warm feeling within her bowels. He withdrew his quickly deflating cock and sat back on the folding chair.

Mr. Genge, however, wasn’t finished.

“Let me at that pussy of yours, Andi,” Mr. Genge sneared.

“Sorry, but that’s off limits. You can have my ass, though.” Andi turned and offered her gaping asshole to him.

“I’m no animal or homo. I’m gonna fuck that little pussy of yours.” The old man demanded. He grabbed Andi by the waist and pushed his stiffening pecker between her labia. Andi twisted and elbowed the old man in the face, causing his mouth to bleed.

Mark stood up from the chair and stood between them.

“Mr. Genge, be happy you got the blowjob. If you want to fuck her in the ass, she’s offering, but her pussy is not an option. Got it?” Mark bowed his chest as come dripped from the tip of his dick.

Mr. Genge’s hard-on quickly faded. “I ought to fire you!” he stammered.

Andi turned and wiped the blood from his mouth. “Please don’t!” She pleaded. “Mark’s not at fault here. It was my idea. I could have waited until his shift was over, but I wanted to have some fun with him. You see, I want Mark. I want to be with him and only him.” Andi glanced at Mark who was listening carefully. “If Mark will stop seeing other girls — if he chooses me — I want him to be the first in my pussy. I’m still a virgin — there.” There was some truth in what she said, although she wasn’t sure which part.

Mr. Genge’s hard-on slowly returned.

“You see, I promised my mom I would wait until I was married to have regular sex. I kinda bent the rules. But I’ve kept my promise all this time. If Mark asks me to marry him… well, you know.” Andi resigned.

The old man turned Andi around.

“Let me see that asshole of yours,” he grinned as he pushed the head of his old cock against her anus.

Andi didn’t hesitate when Mark put his cock against her mouth.

She was a whore, all right. Just like her mom, Jill.

Jill gasped as Brian shot his come in her pussy for a third time. She loved the sensation, the warmth inside of her. He rarely lasted for more than ten minutes at a time, but he could keep her going with his mouth while he recovered.

It had been two weeks since that terrible night. The bruises on her body were gone, and her pussy and asshole both felt normal again. She had only seen Mark, her daughter’s friend, at her home twice, and was hoping she wouldn’t have to see him again. Both times he was at the house, she felt like he was up to no good. For now, though, Mark was a distant memory.

Jill’s pussy gushed as she rode the waves of her fifth orgasm.

“Brian, stop!” Jill panted. “Give me a break. What’s gotten into you?”

“I’ve been away three weeks, I’m horny, and you shaved your pussy again.” Brian said as he turned her onto her stomach. “What can I say?”

Jill crossed her arms under her head as Brian spread her legs. Jill playfully curved her back, raising her ass and causing her pussy to open. Brian’s tongue, thrusting deep into her asshole, was the last thing she expected.

“Oh fuck!” Jill cried.

Brian’s tongue swirled inside her asshole several times before he withdrew and kissed her ass cheeks. He gently kissed the crease where her legs met her ass, and then proceeded kissing her up and down her legs. Jill’s hips gyrated as her right hand found her clit.

Brian kissed the bottom of Jill’s feet, licked and sucked on her toes, and then licked, kissed, and occasionally nibbled on her calves and thighs.

Jill’s ass was raised in the air as Brian’s semen coated the fingers in her pussy. Again, Brian swirled his tongue around her anus. He could tell Jill was enjoying this, and leaned forward.

Jill felt his stiff cock pressing against her folds as he whispered in her ear.

“Do you want it in your ass?”

“If you want.” Jill whispered back.

“No, I want to hear you ask for it.” Brian rubbed his cock harder against her hand and pussy.

Jill paused for a moment. Her handed rubbed her clit faster.

“Yes. I want you to fuck me in the ass.” Jill confided.

Brian positioned himself above and behind her, squatting as he lowered the tip of his cock to her slick anus. He was very careful. Previous attempts at anal sex with Jill had been pleasurable, but he knew the initial penetration was especially painful for her. This time, though, he was able to sink his dick into her ass much easier.

Jill barely moved as he lowered half his shaft into her. Instead of signalling him to wait, she arched her back further, as if taunting him to push himself in just a little more.

Brian could feel Jill’s fingers inside her pussy. She was finger-fucking herself hard. He thrust inside her ass deeper and faster until his rhythm matched hers.

Jill had a flashback to that night a few weeks ago. It was the first time she had ever experienced a cock in her pussy and a cock in her ass simultaneously. The first time hurt like hell and she couldn’t help but feel she had to shit throughout the whole event. But by the fifth or sixth time, she was able to position her body in such a way as to enjoy the double-fuck.

How she wished a fat cock were pounding her pussy right now.

Brian had held out as long as he could. He deposited his come in Jill’s ass in three long spasms, before unceremoniously pulling out his deflated cock. He collapsed on the bed next to her while Jill continued to finger her pussy. Seconds later, Jill’s stomach tightened and come bubbled out from between her fingers. She held her breath for a few seconds and then fell flat on her stomach, slowly bringer her hand to her face.

“What’s gotten into YOU?” Brian asked.

“You were gone for three weeks, I was horny, and I just shaved my pussy.” Jill smiled.

She paused for a minute. She knew he was going to ask why it was so much easier to penetrate her ass this time. Telling her husband that her dildo scavenger hunt for a bachelorette party caused her to end up on the wrong side of town, AND that she was accused of whoring in the process, AND a twisted cop had her service him and at least a half dozen other men with her mouth, pussy, and ass for almost five hours straight as part of her “community service” punishment… was not an option.

“Remember that scavenger hunt I was on — for the bachelorette party?” Jill asked.

“Yeah, I remember.” Brian answered disapprovingly.

Jill leaned over the edge of the bed and reached underneath for one of the toys. She picked one still in its large box and pulled it onto the bed.

“Don’t be angry, and don’t tell anyone.” Jill said shyly. “I decided to experiment.”

“Really?” Brian’s eyes widened. “With this!?!” It was one of the largest dildos in Jill’s collection.

Jill looked at it closely. “No, maybe not this one.”

She reached under the bed again, this time pulling out a toy similar in size to her husband’s slightly-above-averaged-sized cock. “This one.”

Brian breathed a sigh of relief until Jill pulled out another toy from under the bed.

“And this one.” Jill winked at him.

“Isn’t tomorrow night the bachelorette party?” Brian asked. “What are you going to do when you don’t have any more toys?”

“Well, I was going to ask you…” Jill started. “Would you be okay with me keeping one or two?”

“If it makes you happy — and if you continue to fuck me like you did just now — I’m all for it.” Brian smiled. Jill hadn’t fucked him that hard since their honeymoon. Jill kissed him deeply as she stroked his cock back to erection.

“Are you sure your mom got all the dildos on the list?” the bride-to-be asked Andi.

“Yeah, she got them all.” Andi smiled. “Aunt Margaret is going to freak!”

“I bet she’ll take it all in stride. You know some of these women probably haven’t seen a dick bigger than five inches. Heck, I bet some of them haven’t seen a dick in twenty years, period.”

“Is the banquet okay with the strippers?” Andi asked.

“The banquet hall is owned by a woman. I invited her, too. What do you think?” the bride-to-be smiled. “Oh, I almost forgot! Your friend, Mark, even volunteered to dance and strip at the party, too.”

Andi smiled uneasily. She wasn’t the jealous type. That wasn’t what concerned her. She was afraid Mark would turn her on so much; she’d want to suck his cock in front of everyone. She let out a deep sigh as a wet spot formed in the crotch of her jeans.

September 2018
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