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Jamie Harris typed in the user name and password of his account with his favorite online amateur porn hosting site. He was alerted to a new message. He clicked the envelope icon and viewed the correspondence from screen name ‘DLdriller’.

Damn fembunnybttm!!! I wanna get in that ass. Where are you located? I think we stay close.

Jamie fired off a reply with his location along with his email address and the number to his spare prepaid phone. He logged off the computer and hopped in the shower before heading to work at the clinic where he was the administrator. Later that day, Jamie returned to his office and checked his phones. On the touchscreen Tracfone by LG, there was a message from a number he did not recognize. Upon reading the message, he learned that it was ‘DLdriller’ confirming that they lived only 90 miles apart.

The light-skinned bottom with dark chocolate eyes hurriedly fired off a text. It was answered nearly as quickly with a request for pictures. Jamie sent four images – one of his yellow ass covered in soap suds; another featuring him squatting on a dildo; the third was a naked full body shot; and the final showed him all made-up, or wearing his war paint as he called it.

Jamie then received two snaps of his admirer’s body. He turned out to be a brown-skinned man with a nice physique containing a toned chest, thick muscular thighs, and a long dick that curved downwards. Jamie replied telling him how handsome he was and described in detail what he wanted to do with the stud. He sent back a smiley face and said he had to do some things so they would connect later on.

As it was Monday evening, Jamie headed to the dance studio where taught advanced ballet. Jamie studied dance in college, but after spending four years touring he headed back to school to get his master’s in healthcare administration. The pay was much more lucrative, but the work not nearly as fun. Teaching dance kept him sane and allowed him to earn a small income on the side – which helped out considerably come tax season as he could write off trips, phone bills, Internet expenses, and countless other charges.

That night, Jamie was catching up on a reality TV series when, he got a call from his newfound friend.

“Hello,” Jamie answered in his soft effeminate voice.
“Damn, you sound sexy as shit,” the baritone replied.
“Thank you!”
“When we gettin’ up?”
“Soon. Are you coming here or me to you?”
“I can come to you. But it’ll be this weekend before I got gas money. But she works nights starting Friday, so you could come here and kick it with me then.”

“How about I just come there and get a room,” Jamie asked.
“For real?!? That’s wassup! We gon’ get real freaky?”
“Yes sir,” purred Jamie.
“Bet. I gotta go. Stay in touch. I’m for real about Friday.”
“Me too. You smoke.”
“No. I drink though. And I don’t mind if you smoke.”
“Shit, that’s wassup. I’ll hit you later.”

Though the conversation had ended Jamie’s thin eight inch dick was rock hard. He pulled out his iPad and selected one of his favorite porn scenes. He stroked himself while playing with his nipples. All he could think about was having his plowed by deep voiced man. He shot a huge load in his hand then licked it up.

The week had gone by in a very uneventful manner. Jamie packed his overnight bag and hopped into his 2011 light blue Toyota Camry. He headed up the highway. A few miles from the exit he needed to take for the hotel, he turned off to hit the liquor store. He bought a large bottle of vodka, cranberry juice, a flask of cognac, and cola. He paid for the beverages and headed to the hotel.

The pair of them had been texting all week, but the messages were swapped in a frenzy in today. He settled into the room and jumped in the shower where he shaved his legs then oiled up his body afterwards. He replied to the most recent message from his soon-to-be master.

-Room 219
-Bet. Get off work in 30 min. Ima go home & shower. You want sumthin to drink?
-I’m good. Picked up some vodka & cognac already.
-Dat wassup. C u in a hr

Jamie answered the door wearing black leather thigh high boots, a red corset, a pink thong, and a bright orange wig.

“You look so fuckin’ hot. Just like a bitch. Look at that ass,” he remarked as he hugged Jamie and squeezed the cheeks.
“Thank you! You smell great,” Jamie beamed.
“You do too.”
“What something to drink?”
“Yeah let me get some of that cognac.”
“Mixing it with cola. Is that cool?”
“Yeah. Mind if I blaze?”
“Go right ahead.”

Jamie poured the drink as Rob lit the blunt and inquired, “What’s your name.”
“Rob,” he replied.
“What kinda work do you do?”
“Oh I work at Wendy’s and I go to JSU.”
“What’s your major?”
“Criminal justice. What do you do,” he inquired.
“Healthcare administration.”

“So…um…I never told you this, but this is my first time messing around with a dude,” Rob confessed.
“That’s cool. How old are you?”
“Twenty-three. You?”
“Forty.”
“For real,” Rob inquired with disbelief.
“Yes,” Jamie confirmed.
“You don’t look it. Why you sittin’ on the other bed?”

Jamie stood up and moved next to Rob. They began making out while Jamie squeezed his massive erection. Jamie leaned down to remove the member from Rob’s sweatpants. It was an uncut nine inch monster. “Oh my,” Jamie mused before wrapping his lips around it. “Mmmmmm,” he moaned.

“Suck that dick,” Rob ordered enjoying Jamie’s wet mouth.
“Mmhmm,” mumbled Jamie.
“Damn, that shit feels good.”
“Thank you.”
“You might as well take that wig off. We gettin’ wild tonight.”

Jamie removed the hairpiece and threw it on the desk across the room. He stood up and offered to refresh their drinks. As he walked away, Rob grabbed him by the waist and turned him around. Rob stroked Jamie’s long dick and then put it in his mouth. Jamie was in shock. The blow job felt fine but amateurish.

“Ooh,” Jamie delighted.
Rob pulled his mouth away and said, “Just wanted to try that.”
“It felt good,” Jamie replied. “But you don’t have to do it.”
“Cool. Hurry up and get back on this dick.”

Jamie returned with their liquor and started sucking again. Rob removed his shirt. Jamie admired the African-American god of a man. Rob who stood at six-feet-three-inches and towered over Jamie who was on five-foot-six. He picked up the much shorter bottom and placed him on the bed with his ass in the air. Rob pulled the thong aside and dove right in. He licked away while working to remove Jamie’s corset. When the lingerie had been removed he flipped Jamie onto his back.

“I love those perky nipples,” Rob commented before sucking on them.
“Oh yes! Oh yes! Oh God yes,” Jamie squealed.
“I’m ready to fuck you,” Rob announced. “Get on your knees!”

Jamie bounced up and retrieved the bottle of baby oil. Rob took it from him and lubed up his junk. He stroked it as he watched Jamie wiggle his ass and sniff away at something.

“What’s that,” Rob quizzed.
“Poppers.”
“What’s it do?”
“Helps your muscles relax.”
“That’s wassup,” Rob approved as he pushed his dick against Jamie’s anus.
“Oh yeah,” Jamie cooed as his orifice opened to accept Rob’s manhood. “Give me that dick!”
“Take it all in!”
Jamie cried out, “Ooh that dick feels good in my pussy.”
“Hell yeah!”

Rob held onto Jamie’s round butt cheeks as slammed in and out. His tool was quite fat and it spread Jamie’s hole open. He plowed away enjoying every moment.

“You like fucking that boipussy,” Jamie asked.
“Yeah I love fucking your boipussy,” Rob professed while increasing the pressure of his strokes.
“How nasty do you wanna get, baby,” Jamie exhaled.
“Nasty as fuck. I wanna piss on you,” the younger top groaned.
Jamie delighted, “Ooh yes! Piss on my faggot ass!”
“You like that shit, faggot?”
“Never done it before. But I’d love to try it,” Jamie confessed as his ass was pummeled.
“After I nut, Ima piss all over you.”

Rob hammered Jamie and after six more minutes he began to howl.

“I’m finna nut!”
“Oh yes. Nut in that boipussy,” moaned Jamie.
“Shit yeah. I’m finna nut in yo’ faggot ass.”
“Ooh Daddy.”
“Ahhhhh! Argghh! Boipussy,” Rob shrieked.

Rob’s load flooded Jamie’s hole. He could feel the five pulsations that released the hot sticky protein-filled goodness inside of him. Rob wiped the sweat from his forehead. “Take all that shit off and get in the tub,” he ordered. Jamie stripped and ran into the bathroom. Rob aimed at the slutty bottom and began to urinate on his chest. “You want it on your pretty face,” Rob inquired. Jamie shook his head and Rob moved the stream upward. Jamie opened his mouth to let some in.

“Oh my god,” Jamie squealed. “My make-up is gonna look a mess.”
“It’s cool. You’re a faggot anyway. Wash up and get back out here,” Rob said nonchalantly as he walked away.

When Jamie returned, Rob was puffing away and sipping his drink. Jamie oiled up his body then began sucking on Rob’s dick. It grew fairly quickly. This time Jamie sat on Rob’s dick facing away from him. Jamie inhaled his sexual stimulant and bounced on Rob’s love stick as if it were a trampoline. His boipussy slurped and farted.

“Damn that boipussy talkin’ to me,” Rob approved.
“Yes sir,” Jamie smiled still jumping up and down.
“You a cock hungry li’l slut!”
“For you, daddy!”

Jamie rode and Rob reached around to pinch his nipple with one hand and fondle his dick with the other.

“Oh damn,” Jamie wailed.
“You workin’ this dick. You gon’ make me nut again.”

In a flash, Rob picked Jamie up and threw him on his back.

“I’m finna fuck that boipussy like a girl,” Rob said getting on top.
“Please,” Jamie begged.

Rob stroked rhythmically. Jamie reached to pull his down so their chests were connected. They kissed while Rob fed Jamie’s sissy hole. The friction from Rob’s stomach titillated Jamie.

“I’m gonna cum,” Jamie yelped.
“Nut faggot,” Rob commanded.

Rob rose up just in time to see Jamie’s shoot his load half way up his stomach. The sensation of Jamie’s sphincter and contracting anus took Rob by surprise.

“Oh shit, bitch. I’m nuttin’ again,” he hollered.
“Yes! Gimme that nut!”
“Ahhhhhh shit! Ahhhhhh! Oh FUCK. Boipussy,” he barked as his cum rushed in Jamie’s inner sanctum.
“Oh that feels good,” Jamie divulged.
“Shit, Yo’ ass is the truth,” Rob avowed.

They lay there for the next few minutes with Rob’s dick still inside Jamie’s ass. As they cuddled, they drifted off to sleep.

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This is the time that some guy in my geology class blurted out, “Are you high right now?” as class was ending one day. Of course, I was, otherwise I would have delivered the smack upside the head that that kind of lack of discrepancy warrants. Instead, I gave a stupid chuckle, pffft, no, of course not?!? Such a preposterous idea had never been proposed. But I was, and I guess that means I was in with him. Low standards if you ask me, but I’m down. He was cute, a bit juvenile looking, but...

College Sex
2 years ago
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First Online Hookup

Every once in awhile I get horny enough to hop on a male for male hook up site and browse around, luckily for me most of the guys on the website are older so it’s nice jackoff material too. I usually just browse around till I’m horny enough that I’m on the edge of cumming then jack myself off to take care of it. This day was different though. I log in to the website and within about 5 mins, an older man in his 50s messages me asking me how my day was. I was horny as hell that day so I told him...

3 years ago
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The hookup

I walk into the pub and take my usual seat at the end of the bar and wave over the bartender. I order my usual whiskey and look down at my hands. The pub was always busy, full of teenagers letting loose after a day of long boring classes, I hated the noise they brought in but I let it slide considering I was always having dirty thoughts about the young college girls that came in. I scan the room and spot my target for tonight. A young girl at the other end of the bar, she had strawberry blonde...

2 years ago
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Car wash hookup

In my 48 years of life on this planet I have been fortunate to bed hundreds of women. Some might scold and look down upon me but yet others envy it. I have average looks but have always stayed in shape by eating healthy and going to the gym. The past few years I have been approached by more married or attached women than single ones. I have learned that women cheat probably just as much as men or more however they seem to hide it better. I was divorced at 32 and have been single ever since. I...

3 years ago
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My First Hotel Hookup

Recently I was on a business trip and had a free evening. I was content to hang in my room and watch porn and jerk off. I was watching some bi and gay porn and getting pretty turned on so on a whim I downloaded Grindr to my phone. I had it on my phone before, but nothing ever came from it, so to speak.After it finished I opened it up and boom. Thanks to the distance info on the app there was a “DL Married Bi” guy 50 feet from me. Wow! I immediately felt my heart rate speed up. I have never...

2 years ago
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On Line hookup

Last evening after I had my dinner I read my emails then surfed the net for a while. I kept my email open. as I was checking out a few of my sites I am a member at the BING sounded and I saw a new email had arrived. Opening it my heart started to race as I saw it was from an older man I met a few months ago at a truck stop. He wanted to know if I was free to meet up with him for his truck broke down and he was staying at a motel about an hour away. I responded that I would love to stop over...

2 years ago
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CL Hookup

So I had been so horny that I posted an ad to CL looking for Dominant guys to come fuck me while dressed. I posted my ad and waited for the responses to cum in. I got one from this thick Mexican guy and he was really into me. He seemed pretty dominant so I invited him over. I took a shower and got my ass ready. I cleaned it well and used this butt plug that i have that is kind of like a snowman with the largest thickest ball being at the bottom. It stretches out my hole so when he would stick...

2 years ago
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My One Cliche Hookup

I was 20 at the time when I let some friends talk me into being their designated driver while they went out to a karaoke bar. I'm not much for karaoke, but I do enjoy watching drunk people try to sing. So on this particular occasion, I became a bar flower.I made myself comfortable on a bar stool, my legs crossed as a tapped a perfectly manicured fingernail against a glass of coke. I had a good spot in my stool, raised slightly above all the people at the tables in front of the stage. I could...

2 years ago
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High School Hookup

This story takes place when I was 21 working at a liquor store. I never in a million years thought this would happen to me.It was a Tuesday night. I was the only one on shift for the night until closing, which was 11 PM. It was a very slow night. I was incredibly horny that day. I was beginning to think dressing up in very tight jeans, very low cut white top, pink g string, and pink push up bra had become pointless. I had already played with myself 8 times into my 8 & 1/2 shift. ...

3 years ago
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Bar Hookup

This story takes place when I was 19, on a summer night barhopping. I was just getting off of work. It was around 5 PM. I had had a very stressful day. I needed to unwind. I called up my girls asking them if they were free to go out drinking all night. They were all free. As soon as I got home I dressed up in the sluttiest clothes I could find. I put on tight blue jeans, black lacy thong, really tight black T-shirt, and black lacy bra. I dressed up with the intent to draw attention to...

4 years ago
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DRNK HOOKUP

Went on a 5 day fishing tip with some friends to rural PA.First night there I take a ride to the gas station/convience store for beer.As im walking into the store im approachd in the parking lot by a middle aged,obviously Dr**nk women (slurring),as she comes forward I can smell here alcohol breath,she puts her hands on my wrists,(which was weird) and asks me if im going to Marshalls Creek.( 20 minutes away).I say no and continue into the store.I buy some beer and exit the store,now in the lot...

3 years ago
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CL Backyard hookup

Had a nice young BBC contact me thru my ad on CL . It has been awhile since I had a nice hard cock so I was very horny for some dick , especially BBC! Got cleaned up inside and out , lubed myself up good . We agreed to hook up in my backyard , nice dark discrete , covered from view from the front and a back wall that is head high , neighbors on all 3 sides if they actually were awake at night and went into their backyards would have a straight view from both sides...I absolutely love hooking up...

3 years ago
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My first non internet hookup

If you are new to my stories, all me stories are true. I write the stories to document my past sexual exploits. Some of the details have been changed to protect the guilty.In my first job after college, I lived in a far suburb of a major city. There wasn't much to do in my town so I often traveled to the city for fun. On one particular weekend, my company had a work function in the city. My roommate and I decided to make it a weekend and to get a room in the city. A lot of my coworkers had the...

2 years ago
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First CL Anon Hookup

I had been fantasizing about meeting up with another guy for sex, and sucking cock for the first time. I'll save the "why" for another story; suffice it to say I had been thinking about it for a while, and had jerked off a fair amount while browsing the m4m personals on Craigslist.One weekday morning for whatever reason I had the day off. I plucked up the courage to respond to an ad posted by a guy in his late 40's who worked from home during the day. One of his ad pictures was a of...

3 years ago
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Random Ex Hookup

I got pretty lucky this weekend. I hooked up with an ex that I've wanted to fuck againA long story short, she cheated on me at the very end but I was already out of there. I was involved because I helped set her up with a guy on xhamster. She was anti-porn but I caught her on here cruising pics, vids and the dating sites. So, I wanted to see if she'd cheat and helped a guy hook up with her in exchange for some pics and eventually he did something similar for me.Anyhow, I was meeting a buddy...

2 years ago
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Caleb my Fantasy hookup

I was at the adult bookstore the other day just checking out the dildos and such not really looking for anything. While I was checking out a video of a guy sucking a hot cock a voice behind me asked if I enjoyed sucking to which I replied I was. He introduced himself as caleb and after a few minutes of small talk he asked if I was interested in going into a booth with him and demonstrating my sucking skills. After looking at the bulge in his pants I quickly agreed. We walked into a booth and...

3 years ago
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My gay CL hookup

A few weeks ago I had answered a personal ad from a gentleman who was looking for some companionship for the day. After exchanging a few E-Mails we had agreed to meet at a local starbucks for a cup of coffee and some chat about what we were looking for and all that good stuff. After we finished our coffee we both wanted the day to progress so we went to the nearest goodwill store where he bought a dress for me to wear and than stopped at walmart for some undies. On the way to his house I had...

3 years ago
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highschool party hookup

she took me by the hand and lead me upstairs, her hips swinging so sensually. every flirty step she takes swings her miniskirt bouncing and swaying back and forth just enough for me to peak under and see the curvy bottom of her ass just where it meets the top of her thigh. it was mesmerizing. watching her ass bounce just inches from my face, that lacy thong rubbing between her legs as she steps up left then right then left then right again. her skin felt so soft as i ran my fingers up and...

2 years ago
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A Stoned Hookup

So, to cut the long introductory indian sex story short, I met this guy on Tinder. We chatted for a while and . This guy introduced me to weed. We met a few more times and smoked weed. I was still learning how to smoke. It was quite risky to do it in open. So he suggested that he’ll arrange some pg room where I can get real high without giving a second thought. So, the day was decided & I went there. It all started with some casual talk, while he was rolling up some joints. I was literally...

3 years ago
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The hookup

Sipping my drink I look around nervously. I start to wonderif he will even show. I am almost ready to leave when I see him. Walking into the bar so full of egotistical confidence it was almost sickening. However there is no denying that he is attractive. Standing at the height of at least 6 foot and even with clothes on I could see that he had a hard body from working out. His dark hair slicked back and I wonder how he had managed to make it look so damn good. I can’t tell from where I am...

Straight Sex
3 years ago
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A Couples Online Hookup

As told to me by a friend : Rob and Jenny pulled through the Fields Corner section of Boston's Dorchester neighborhood in their BMW knowing the street to turn onto was almost upon them. Rob took the left off Dorchester's main thoroughfare looking at the streets knowing he would be taking another left after passing two streets. And his GPS sounded off on that third street. They both were now focused on house numbers and saw quickly the one they sought. And just like the man they were meeting...

4 years ago
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The Hookup

It was three years ago in the beginning of July, only a handful of minutes past 4:00 a.m. when Tom (not his real name) replied to my Craigslist personal ad that I had posted in the T4M section. I posted the ad along with a few clean but sexy pics an hour earlier, asking if anyone was awake and horny. I had begun to think that nobody was up at this ungodly hour when a few replies came dribbling into my email. I rarely posted ads looking for sex. When I had tried before, they would get flagged...

2 years ago
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The Hotel Hookup

Working Up The Nerve I had never done anything like this before; it was risky hooking up with someone you met on an app, especially for me. He could leave me bloody and bruised on the side of the road after taking all my money; hell it could be a group of backward thinking Neanderthals wanting to kill me. Or worse yet, he could destroy my life in another way; I was deeply, deeply closeted. No one knew I was attracted to men. I had spent the better part of my 29 year old life casually dating...

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