The Dangers of Glory Hole Dating

Hi there reader. This is a new story of mine, one of many attempts to break out and try to write in a very different category to the ones I'm used to. I will be giving several categories a go, many of which I haven't ever written in before, or in some cases even thought about. I hope you enjoy the experiment!

*****

"hey guys, sexy chick willing to give out a bj for a little reward...hot mouth, DDF, fully discreet and anonymous. put "bj reward" in the subject to prove you are real."

It seemed like it would be another fake craigslist ad for Michael, but he answered it all the same, using one of his anonymous email addresses. "Why not," he said out loud to himself, "there's no harm in it." He kept his reply short and simple:

To: "bj reward"

Subject: bj reward

hey, young guy, tall, fit, clean and would like to know more, happy to stay anon, hope to hear back soon.

He sent it and leaned back in his chair. It was another boring night in a long, boring dry spell that had lasted since he left last girlfriend all those months ago – just because it had been the right thing to do didn't make it easy. He didn't want to string her along anymore; he cared about her too much to let her think there was hope when there really wasn't any.

Of course, now he had very little fun in his life. He worked whenever he could to earn money, but most of it went to helping his mother Lindsay pay the mortgage. She worked all the time herself, so in the end the little free time he had was spent eating alone at home, with hardly any pocket money to go out and socialise. As a result, Mike spent every other night browsing sites like Craigslist, looking for people interested in hooking up. It was like a taboo of sorts, seeing who might be keen in nondescript meets, and at least with his mother working late nights and his sister now in college he could enjoy having the whole house to...

What the...? He had a reply already. This seemed too suss – it had to be spam. He clicked on the reply and leaned forward to read:

To: replier

Subject: RE bj reward

hi, how much r u willing to pay? low on $ and got some big fees, not running a charity, can maybe sort something out, had a few responses but mostly creepy old guys...how old r u?

Well, she seemed to be genuine, now the question was...what to do? Truthfully Michael just didn't have a lot to spare, and he certainly didn't want to splash out massive amounts on a random bj. He thought about it and carefully wrote back:

To: "bj reward"

Subject: RE bj reward

i'm 23, not creepy just lonely, but not super rich...work something out maybe? can be flexible, what are you looking to get?

He paused, thinking about it before he hit the send button, wondering what he would pay; at the most it'd be fifty, and even that would be hard in one go, there were bills and fees to pay, and there was no way he could afford much this week, but she might not be willing to wait. Perhaps if he...

Wait, one go...that's it, he thought to himself. Maybe I could convince her to...yes, why not? He continued to write:

if you want...instead of only one big payment...maybe we could meet a few times, little payments each time? could end up giving you a lot more in the end that way, im just little short this week so yeah...what do you say?

also, what do I call you?

He sent it and got up, stretching as he headed to the kitchen. He had fixed himself some dinner since once again his mother wasn't going to be home. Tossing a plate of pasta in the microwave, he sat and contemplated his situation.

More than once Michael wondered if his mother was secretly going out on dates instead of staying late at work; his father had left years ago, and his mother was still a fairly attractive woman and in good shape for forty three, with not a strand of gray in her blonde hair, long legs and an hourglass frame. He knew she deserved someone for herself, and it was a bit lonely at home with just the two of them now that his sister Grace had moved out.

Mike stared up at the family photograph on the wall, taken the day Grace went off to uni. She and their mother were about the same size, with the same blonde hair that seemed to run in the family and slender builds, so they had often gone shopping together or even borrowed each other's clothes. But Grace was a busy nineteen year old student, spending most of her time studying or socialising with people at events, making connections – networking, she called it when they spoke on the phone. Mike suspected his mother missed the time they used to spend together, which then made her miss Grace even more.

Thinking about it more now, Mike secretly wanted his mother to be dating in secret, spending her evenings doing her own socialising, but she had always been a bit of a workaholic. Mike had seen divorced parents lose it when they sat around with nothing to occupy themselves, so at least his mother wasn't going down that road. His mother was smart, and definitely enjoyed her work, and as long as they kept the bills paid she seemed happy enough to just keep going through the motions.

The microwave broke his concentration with its shrill beeping and he walked back to his room with a hot plate of food. Amazingly, there was another fast reply waiting when he got back to his laptop. Even more amazing was what it said:

To: replier

Subject: RE bj reward

interesting idea, if i agree ull end up paying more that way. u ok with that? maybe like $20, four or five meets? Can spread it out, do other stuff or watever, but all anon plz.

is good ur young ;) can be free tonite if u want...

p.s. u can call me jessie. u?

Michael couldn't believe it. This was happening, it was real!

Hold on, he thought. Are you sure you want to do this? Meet up with a random girl you haven't even seen? Despite how lonely he had been lately Mike wasn't as confident now that he had to make a clear decision. Unfortunately after weeks of work, sleep and repeat, his mood got the better of his common sense and he decided to commit before he got cold feet.

To: "jessie"

Subject: RE bj reward

sure, can be free tonight, happy to keep discreet. how do u want to do it then?

He almost hit send, then added one more thing at the bottom.

you can call me james

Mike sat back and waited for the reply, digging into his food and wondering if he could go through with this. Something about the whole scenario seemed really kinky to him, and it turned him on. He didn't have to wait long before she came back.

To: "james"

Subject: RE bj reward

cool! :) u have to wear a condom tho, dw ill bring them.

i have a place...there are special booths out the back of a bar in the north part of the city...that old historic place called swinging jacks? near the bathrooms down a corridor, ill be in booth 3, go in booth 4 and tap the wall three times, ill tap back the same way if im in there, then pass ur $$ thru the little hole between them.

oh and tap wen ur going to cum ok? ;)

ill be there in half an hour. c u soon james ;)

So that was her plan then. Well, with mum out I'm not going to be getting up to much here, Mike thought as he quickly finished his meal and pulled on a clean shirt. He was only twenty three and yet his social life had ground to a complete halt already. He looked at himself in the mirror briefly to make sure his hair was right.

Mike had a fairly youthful appearance, with a clean shaven face and the same blonde hair that ran in the family, although his was closer to brownish blonde, much darker than the rest of his family. He had his father's slightly olive skin while his sister and mother were both a little more pale, and he was regretfully only a fraction taller than any of them, and being from a family of skinny body types he wasn't a whole lot broader either.

Sure, excessive amounts of gym training would fix that...but Mike wasn't one of those guys. He didn't have dumbbells in his room, he didn't spend a few minutes smashing out reps on the chest press and then walk around the house with no shirt, he didn't spend a lot of time being sweaty from exercise and he definitely wasn't six foot with perfect abs.

How many people really look like that anyway? He also didn't care a great deal. No one ever told him he would look better buffed up, and living in the gym just to get a few extra muscles seemed like a really superficial waste of time. He still helped move furniture, he did the chores for his mother and he could hammer a nail into place without hitting his own hand. That counted for a lot more than "mad gainz".

Mike combed his hair frantically to make it stick down but, in the end, gave up trying and figured she wouldn't be able to see him anyway. He brushed a spot of dust off of his t-shirt and sprayed a bit of deodorant, wagering that even if his mystery date couldn't see him at least she would appreciate his hygiene. Glory holes weren't something he had a lot of experience with but he knew enough to realise she would be completely hidden too. As long as she actually is a girl I've got no problem with that, he thought to himself as he grabbed his car keys, pulled on a jacket and headed for the door.

–-

It was a relatively short drive to the city from his house, and not much further to the old bar known as Swinging Jack's. He hadn't been there often himself but he knew it had a reputation for being the party animal hangout. Most young guys and girls either started or ended their nights at that place, with a massive selection of drinks, a huge dance floor and an upper level filled with pool tables and a karaoke machine on stage.

The place had some history to it. It was named after a famous bank robber and a hooligan who tormented the local cops back in the 20s and often used to spend time there when it was just a little old tavern. Some said that he was a swinger, always seen with a different girl on his arm, hence the name but the story of his death told a different tale.

Outlaw Jack met a noble and tragic end in a gunfight with the cops at his safehouse one day after being caught at the scene of a heist, and although the historical records say he was shot and found amongst the bodies of his crew, legend had it that the cops took him alive, then executed his whole gang and hung him on the spot for all the trouble he caused them. They say he died with a grin on his face, pissing off the lawmen one last time while swinging from the branches of a tree.

It was pretty busy for a Thursday night; the owners were adaptable enough to offer cheap drinks which usually got people out despite the loom of work in the morning. Mike pulled into the car park and hopped out, heading inside to escape the hot summer air. The old doors creaked open and the sounds of lively patrons washed over him as he made for the bar, grabbing himself a beer and looking around, wondering if any of his friends were out tonight. He knew most of them wouldn't be, but he couldn't think of anything else to do at the time. He was nervous.

Pulling out his phone, Mike took a swig of his drink and accessed his email and re-read the last message. Booth four, half an hour. I could wait out here, but guess I should just go in now. Mike quickly downed his drink and, with the help of the liquid courage, he moved through the crowd to a small hallway at the back of the room.

Mike found himself looking at a darkly lit corridor, with doors lining the walls on either side of him. He spotted booth 3, the light above the number indicating it was already in use, so he moved to the one next door and went in, locking it behind him and hoping Jessie was the one in there.

The booth was small, but at least it was bigger than an airplane bathroom. There was a chair in front of a T.V. on the wall, with a little coin slot on the side of the wall next to it. He took a look and put some money in, turning on the screen which started playing a gangbang porno. On one side of the booth, the wall that it shared with booth 3, there was a little flap and behind it, a round, smooth hole, the size of his hand with his fingers outstretched. Mike heard movement on the other side, so he tapped slowly three times.

After a pause Mike heard three taps back, so he took out his wallet and pulled a twenty from it, moving the flap and holding it up to the hole. The flap on the other side moved and the money disappeared, and then was replaced by two slender fingers with long feminine nails and bright red nail polish.

That did it. Unzipping his pants, Mike took his cock out and gave it a few strokes, waiting until it was fully erect. With the porno playing in the background and the girly fingers beckoning him it didn't take much. When he was ready, he slowly moved forward, feeding his cock into the hole and waiting anxiously.

He immediately felt a soft, warm hand wrap around him, rubbing him a little before a set of wet lips kissed the head of his cock. Mike half-jumped, eliciting a girly giggle from the other side of the thin wall. He felt a rubbery condom being slipped over his head and down his shaft, then as her hand moved back and forth, the girl's lips moved forward and engulfed the head of his cock.

Mike gasped with pleasure. Jessie's mouth was warm and soft, her tongue dancing around his member as she moved her lips up and down his cock. Slowly but surely she worked her mouth further down him, taking at least half of his length before she started bobbing her head faster, her hand stroking the base of his shaft. Mike pressed his hands against the wall and pushed his hips forward, begging for more. With a smooth motion the girl deepthroated him suddenly, pulling back to resume sucking the first half of his cock.

Holy shit, Mike thought to himself. This girl is amazing! Mike's last relationship had ended a few months ago and since then his luck had been pretty bad, but now he was getting the blowjob of his life, and he didn't even know what she looked like! Whoever she was she had natural talent – and must have had a fair bit of experience behind it too!

Jessie's lips slid rapidly up and down his shaft, keeping it wet with saliva as she sucked him hard. Her hand was stroking the base of his cock as well, pumping him fast without squeezing too roughly. Mike didn't know if she realised it but everything she did was working beautifully. Her tongue slid down the underside of his cock as her head moved forwards and backwards on him, her mouth forming a perfect shape around him. Jessie's fingers were soft and her mouth was warm and wet, and before long Mike could feel himself getting ready to burst. Just the thought of cumming in her perfect mouth started to send him over the edge.

Mike quickly tapped on the wall, almost forgetting the plan. The mystery girl gave him a squeeze and swallowed his whole cock, gagging slightly as she held her lips to the base of his shaft, moaning quietly. Mike moaned as well and closed his eyes, feeling his cock twitch and pulse as he shot jet after jet of cum into the condom, feeling the girl's lips quiver as she kept herself from gagging on him.

When he had calmed down the girl pulled back again, gasping for air and rubbing his cock with one slender hand. She peeled the condom back and he felt her wipe him down before giving his slowly softening member a few strokes. He heard her whisper "thanks" through the hole before she gave him another quick squeeze and kissed the head of his cock again, letting him go to withdraw from the hole and put himself away.

"See you soon?" she asked.

"Sure," Mike whispered back, before making his way out to the bar.

Mike felt conflicted as he drove home that night. On the one hand it was a fantastic blowjob, and definitely a girl on the other side of the wall. On the other hand, he knew she was only there because he was offering money for each meeting. He thought about it all the way home, right up until the moment he fell asleep.

–-

For the most part, Mike went about life as normal over the weekend, but that was about to change. A bad couple of days at work and Mike found himself on another Thursday outing, this time on a rubbish date with a girl who was more interested in tumblr, instagram and twitter than in actually interacting with people in real life. Mike knew that as hot as she might be, no chemistry meant no hope and a pretty rotten screw even if he wanted to go there.

He left her to pay her half of the bill feeling unwanted and grumpy. It was only 8:30 at night, so after making his way home he sent a short email and sat with a beer at his desk, waiting impatiently for a reply. When it did come his mood started to lift.

To: "james"

Subject: RE bj reward

hey, glad i heard from u ;) same deal as last time? ill c u soon ;P

jessie

By the time Mike got to the bar he was looking forward to a good blowjob and feeling better than before, but he still couldn't shake his generally down mood. He hadn't put money on getting laid of course, but he had really wanted to have a positive outcome to his date, not another jab to his confidence. Jessie didn't really count as a date but he reasoned that he would spend about as much on her as he would taking a girl out to dinner, maybe even less given how expensive most restaurants were.

He found the booth empty and the one next to it occupied again, so he closed the door and tapped on the wall. Three short taps back and slender fingers poked through the hole again, beckoning him.

Mike offered the money to the hole and unzipped his pants, eager to get going now that he was here. The note disappeared and he fed his cock into the glory hole, feeling those soft fingers stroke him gently. As before, a condom slid over him and he was taken into her hot, wet mouth.

It was as good as Mike remembered, maybe even better tonight since there was no first-time anxiety. Jessie sucked on him hungrily, trying to take all of him into her mouth at once. She wasn't bad at deepthroating, but still had a bit of trouble with him. Her hand jerked the base of his cock as she pulled back and sucked on the head, her lips sliding up and down his shaft wetly.

Mike pressed himself against the wall and hugged it tightly, not wanting to pull away for anything. Jessie was fantastic at giving blowjobs, and the thrill of the glory hole made it all the better. He felt her lips slip halfway down his cock and he gently pulled back and thrust into her mouth, her fingers relaxing their grip a little to allow him to fuck her face. Jessie started moaning and Mike could feel himself getting close to cumming already. He sped up a little and heard little gulping noises on the other side of the wall as Jessie swallowed his cock, her lips working back and forth.

Mike reached the breaking point and tapped the wall quickly. Jessie's soft fingers wrapped around him and jerked him off as she sucked hard on his tip, her moans getting quiet as she concentrated on sucking him off. Mike moaned and pushed into her mouth as he shot his load, feeling her lips tighten around him. Jessie moaned again and Mike gasped with pleasure as her fingers stroked him lovingly, coaxing every last drop of cum from his cock. When he was done she peeled the condom off and wiped him clean again, giving his bare shaft a few strokes.

"Thanks for this," he said. "I really needed a break." She didn't reply, but her warm lips pressed against the end of his cock and slowly took a little of him into her mouth, giving him one naked suck before she pulled away, kissing up and down his shaft sweetly.

–-

A month passed and Mike had gone back to the glory hole three more times each Thursday, and each time Jessie had caressed his shaft and made him cum hard for her. Each trip started to go for a little longer, with Jessie teasing out his ejaculation, getting him close and then knowing just when to back off, to play with the head of his cock and make sweet love to it.