The Dangers of Glory Hole Dating

Jessie started to talk a little more too, telling him how much she liked sucking his cock and how lucky she was to get him and not some creep. Mike had reached what he felt was the quota for their arrangement, but their meetings had become less about keeping his promise of money and more about how good the blowjobs were. He even started wondering who Jessie really was; he didn't even know her age, and although she was probably the same as him she could easily be older and he wouldn't have a clue.

Sometimes Mike got little snippets of how her day had been, or what sort of mood she was in when they met, just by talking before and after the blowjob, and he shared the same with her. It made things more relaxed that way, and gradually she started letting things slip in her emails too, going on for longer than it normally took to organise a meeting time.

What Mike had managed to figure out was she was a reasonably normal person who was short on cash despite working all the time, which at least meant they had something in common. She also loved sex in every form, but wasn't attached at the moment. It seemed like a strange way of enjoying sex, especially as he always felt like sex was best enjoyed when it was a more personal experience, but in a way he thought it was good that she was honest about herself.

The one thing he didn't know was whether she was seeing anyone else this way, but past experience had made him too afraid to face the answer. One of Mike's first girlfriends was an attention seeker who demanded more from others than she was willing to give, not to mention more than she was worth. That particular relationship ended with her fucking random guys here and there and pretending like it was everyone else's fault, and it had left a mark on his ability to trust.

Jessie, on the other hand, felt different in some way, although Mike couldn't put his finger on why he thought that about her. Maybe it was that she never seemed in a rush to get him out. maybe it was the way she always appeared to be sitting at home waiting to hear from him, rather than sitting in the booth for man after man to visit.

A quiet Friday at home after not seeing her for a week had Mike thinking about her a little differently. Breaking their Thursday cycle was affecting his mood a lot more than it should have, and he started thinking of her less like a stranger who could be any age, height or gradient of crazy, and more like something else entirely. To get his mind off his mystery girl, he called the boys and got a poker night going, banking on a bit of friendly distraction to ease his mind.

"So no word from Ruby?" Josh asked him, taking a look at his cards and calling. Jeremy folded, so did Luke, but Phil called, glancing at Mike. Josh had been referring to his last girlfriend, the one Mike had chosen to leave despite how good things were. He knew Josh had only his best interests at heart but it was the last thing he needed to talk about.

"None that I am replying to," Mike said stiffly, calling as well. It was dangerous to be seen betting in a bad mood, but with an ace and queen of diamonds he felt comfortable enough to keep going.

"We know she was pretty special," said Rory, who called and laid out the flop. "It's just a shame, man. And you never seem to talk about her, so we were just wondering how things were." The others all nodded, agreeing. This wasn't what he expected when he invited them around for a quiet night. Mike focused on the cards and tried to ignore their stares. Ace of clubs, four of diamonds, eight of hearts, nothing too fancy. Josh checked.

"Listen, if you want I could introduce you to someone," Luke chimed in. "A friend of my cousin. Meghan's basically part of the family, so I know she's cool. I mean, she just got out of a bad relationship herself, and we're all kinda busy getting ready for my cousin's wedding, but who knows? Maybe after the wedding you'll hit it off and it'll cheer her up."

"I might take you up on that one day, Luke, but I really don't have a lot of time to date right now...I need to take more shifts so Mum can have a break, she's working flat out to keep the bills paid and I think it might be starting to affect her. She needs a vacation."

"It's cool, just...you know, don't burn yourself out as well. We all know what you're doin' for your Mum, but giving up all your spare time? That's a tough choice to make."

"Life is all about tough choices," bragged Phil, laying out a stack of chips. "Raise 100." He looked pretty confident, but Mike knew that Phil was a bit of a show off. Sure, you couldn't always tell exactly how much better or worse his hand was than yours, but if he had the absolute worst hand and bluffed or when he had something super good, his mouth would twitch and give it away.

This time Phil wasn't bluffing, Mike just didn't know how good his hand was yet. He himself had an ace and a queen, giving him a pair of aces and the next highest card on the table. Rory obviously didn't think it was worth staying in and folded, but Mike wanted to give it a shot. He called, Josh called and Rory laid out the turn card. A queen of clubs.

"150," said Phil, raising the stakes. Mike knew Phil was very proud of his poker skills, but that was a little too quick. Phil was eager and accidentally revealing too much about his potential hand. Even still, with ace and queen pairs now on the table Mike decided he wanted to play the hand out, if only to challenge Phil.

"Call."

"Sure, I'll call," said Josh, who generally could afford to play for fun and never took things too seriously. Each of them had thrown in twenty five bucks, so while there was money involved the stakes weren't that high, and if all went wrong Mike would simply go home and get some sleep.

"Here comes the River," said Rory, pulling out the final card. Mike couldn't believe it: a queen of spades. He now had a full house of the two highest cards on the table.

"200," said Phil. Again, fairly quick off the mark. So whatever he had was made better with another queen. Could he have pocket aces? Mike didn't think that was it, but something similar...trips maybe, or a queen himself. Either way, Mike knew no matter how good Phil's hand was, he had an incredibly good chance as well, and had to take it.

"Raise," he said, throwing twice the chips out. Josh wasn't ready to go for it and folded, and Phil looked surprised, but also a little smug; he probably thought Mike had only just gotten something good with the second queen, and was convinced he still had the better cards.

Poor Phil. Mike was getting a feeling that whatever Phil had, it couldn't beat his own hand, and Phil was now caught in the unfortunate trap of seeing his best possible outcome on the table. There was no way he could pass that up. It was incredibly bad luck.

"I call," Phil said, and threw down his cards: a pair of eights, making a full house of three eights over two queens. He smiled and Josh whistled, realizing what a reasonable hand Phil had even before the queens came out. Then Mike, his suspicions confirmed, turned over his own cards.

"Er...a better full house, queens over aces," said Rory hiding his grin, sliding the chips towards Mike. Phil's face fell, and a moment later went red as he became aware of Mike's good fortune and his own fate. Mike said nothing, partly because if he had opened his mouth, he might have said something about calling bluffs, reading people's raises and how half of everything is luck.

"Had an ace and a three, man," said Josh to Luke. "Came close to losing a fair bit there didn't I?" The others laughed, but neither Josh or Luke looked at Phil when he said it.

–-

As it turned out, Mike won the game after an all in with Jeremy and Rory, and when the guys had left Mike jumped on his computer and sent an email. It wasn't mushy or worded in any special way, but it was clear on its intent. The fact that she replied at such a late hour surprised him, but it was exactly what he had hoped for.

To: "james"

Subject: RE bj reward

Hey james ;) ur up late! didnt know if id here from u again...glad i did tho ;) im free right now actually, meet u in about 25mins, that ok? have to get condoms, im all out.

looking forward to seeing u...

Jessie

Mike gathered his things and headed for the car, popping his winnings in his pocket. He noticed his mother still hadn't come home yet, and wondered how it might look if he got back later than she did.

–-

Three taps on the wall, followed by three taps in return.

"Hello again," came the voice through the hole. She was definitely keen to be there, he could tell.

"I'm glad you were free tonight, I really wanted to meet you again," Mike said, unzipping his pants. She giggled and waved her fingers through the hole, her nail polish glinting in the dim light of the booth.

"Well I'm glad to hear it," she said happily. There was a pause, and Mike heard a slight change in her voice. "I really wanted to meet you too." Mike was momentarily stunned by how shy she sounded just then, and in the silence he took out some of his poker winnings and slid them through the hole.

"Wow...wow! This is a lot more then normal," she said. "How come?"

"Well, I had a good game of poker tonight," he said casually. He got no reply from Jessie and wondered what she was thinking, then he stopped worrying as those soft fingers slid through the hole to beckon him closer. He moved up to the wall and gently eased his cock through, feeling her warm hand wrap around it instantly. For a moment she only stroked it, feeling the smooth length of his shaft grow in her hand, then Mike felt hot, wet lips suck gently on the tip of his cock before pushing all the way down him.

He gasped as Jessie took him into her mouth, her tongue swirling up and down his shaft and making him wet with her saliva. Her hand gently jerked him off at the base of his cock as she sucked on his head, her lips moving back and forth slowly. Mike loving the feeling of her mouth without protection and was starting to really get into it when he felt her pull all the way off and heard a condom wrapper being opened. As nice as it had felt, she obviously still wanted to use them.

"I don't mind finishing with a handjob," he said through the hole. "If you don't like the taste of cum, that is." Jessie paused.

"It's not that I don't like it," she said slowly, "it's just that I've had a few bad experiences recently. Last time I swallowed was with a guy who didn't tell me he was close and it tasted disgusting and I nearly choked on it." She slid the condom over Mike's cock and gave it a few strokes. "It's not that I don't trust you, it's just...a personal thing. Maybe for the right guy..." she stopped talking suddenly and took Mike deep into her mouth.

Mike gasped again and pressed himself against the wall. Jessie had never been able to deepthroat quite that quickly or even that well before. She held it for a second longer and pulled back as she started to gag, her hand holding some of his shaft as she sucked on the top half, bobbing her head fast.

Jessie seemed more aggressive and hungry than usual, and Mike was loving it. He began to thrust gently into her hand and felt the tip of his cock slide in and out of her lips, her tongue flicking against it with each push. Jessie's attention shifted and her head stopped moving as she focused on just being a hole for him to fuck. Mike heard her moving around in her booth, the clear sound of material being pulled off coming through the hole. Then she came to life again, pushing her head down his length to suck as much of him as she could as her hand started to jerk him off, moaning quietly on her side of the wall.

"Oh fuck," whispered Mike. "I don't think I can last long tonight," he said to her, and Jessie sped up even more, her moans vibrating his cock to give him greater pleasure. She was really getting into him tonight, making noises like he hadn't heard before. Jessie was sucking his cock nice and hard and sliding her tongue over his head as if she couldn't get enough of it, and her own pleasure and excitement seemed to be at the boiling point.

Mike could feel his release coming already, amazed that he could meet a girl this talented. He still didn't even know her age or what she did for a living, but the anonymity gave it a certain excitement and she was sucking him like a pro. Jessie deepthroated again, her almost reaching the base of his shaft as she took him down, gagging once, then twice before she pulled back and coughed, stroking him faster. Mike tapped on the wall as he felt his release coming up, but when he did she stopped stroking him and pulled away.

Mike waited, on the edge of cumming and wondering where Jessie was, when he heard more movement in her booth. Suddenly he felt fingers on him again, but from a different angle, as though she was standing up next to the wall.

"Pull away," she whispered, her voice strained as though she was out of breath. Mike withdrew his cock and knelt down to the hole, Jessie's fingers encouraging him to come closer. He shuffled in and gazed through, wondering what was going on. To his surprise he found himself staring at pink, wet folds between a pair of pale thighs. Jessie was showing him her pussy!

"I need help," she whispered to him, her fold shivering slightly. Mike could see she was clean shaven, and that she was very wet already. She must have been playing the whole time, he thought to himself. The thought turned him on even more and he put his fingers through the hole as Jessie slowly moved closer until her belly touched the wall, her lips pressing against Mike's fingers. She was warm, very warm, and silky smooth to the touch.

Mike wasted no time and ran his fingers up and down through Jessie's folds, hearing her moan as he did so. He stroked her over and over, each time rubbing in a different direction as he dragged his fingertips past her entrance and all the way up to her clit, then changing direction and going back down again.

"Oh god," she moaned, pushing her pussy against him. "Rub my clit again, please?" She was pleading with him. Mike obliged and let his fingers move up through her wetness to her clit, rubbing circles around it gently at first, then getting faster as she panted opposite him.

"Fuck yes, do that again," she breathed, starting to shake a little. Mike felt her legs twitch, like she was about to collapse, and flicked his wet fingertips back and forth over her clit. She gasped loudly and he felt her body press itself against the wall, her pussy dripping wet as she angled her hips to rub against his fingers. "Keep going, ohhh...I'm almost there there, do it again!" she yelled, and Mike did so, rubbing furiously on her little bud. Mike felt her thighs clench together around his fingers, and he rubbed her clit harder as he felt her reach the edge.

"Oh, fucking hell! Ahhhh...!" Jessie came hard, her pussy squirting a little and wetting his hand as she squeezed him, her pussy shaking madly. Mike almost came himself from the rush of excitement, his cock straining to burst now. Jessie's moans slowly subsided after a few seconds, her shivering body slowly calming from her orgasm. To emphasize his predicament Mike tapped the wall again and Jessie slid away from him, his fingers slipping from between her thighs followed by a satisfied gasp of pleasure.

Mike withdrew his fingers and stood up again, sliding his cock through the hole. He had barely put it in when Jessie's mouth closed over him, sucking him hard and fucking his cock with her lips. Mike held his fingers up to his mouth and tasted her juices, and with a deep suck from Jessie he groaned and came hard, feeling his shaft pulse in Jessie's mouth, her lips and tongue pressing against the underside of his cock, each spurt squeezing past her soft red lips and adoring tongue.

Jessie kept his cock deep in her mouth for as long as she could, gagging as his head pressed down her throat, only pulling back after he had finished cumming and was starting to calm down. She pulled the condom off, and this time instead of wiping him down, she took him into her mouth naked and sucked him hard, her tongue running around his head. Mike almost came again, but then she stopped and stroked him gently, laying kisses up and down his shaft. Mike could feel the vibrations from her body through her hand as she knelt before him, and he could almost collapse himself after treatment like that.

"I...I can't stop my legs from shaking," she panted, her hand not letting him go. Mike laughed shakily to himself.

"Glad I could help," he said, and he meant it. Jessie didn't reply and for a moment Mike could only hear the sound of someone trying to dress themselves with one wobbly hand. "Would you like a hand there?" he said, pun intended.

"No, no thankyou," she replied quickly, almost sounding panicked. "I, I'm sorry, I have to go," and with that she let go of his cock and he heard her door bang open, the sound of fancy work heels on the floor as Jessie ran from the booth. Mike quickly pulled his cock back through the hole and did himself up, but it still took him long enough to make himself presentable for her to be completely gone when he reached the almost empty bar room.

Dashing out into the car park, Mike thought he saw a hatchback pulling out with what could have been a woman inside it, but then as he raced further into the lot he saw the brief glimpse of tail lights as another vehicle sped away around the corner, disappearing into the night before he could tell what it was. Either way, he didn't see enough to know which car was Jessie's. He'd lost her.

–-

The next day Mike hopped in the car and made his way down to the university campus to meet his sister and his cousin. He had slept well, despite worrying about Jessie's reaction to their meeting last night. He was feeling somewhat protective of her and couldn't work out his own emotions, and as much as he had wanted to stay home and wait for an email he had promised he would keep in touch with his family. His mother couldn't make it, of course; even with all the extra late night work she had been doing she had decided to work Saturday mornings. More of a distraction than for money? Maybe. Time would tell.

"So how are you? It's been ages since we've hung out together," Lily said, smiling at him. Mike's twin cousins Lily and Caleb were Mike's age and had lived next door when they were growing up, so when everyone started moving out as young adults they had tried their hardest to stay in touch. Mike had even worked with Caleb for a short time when they were teenagers. They were all like brothers and sisters really. Lily's dark red hair whipped around in the breeze as Mike weighed his answer, considering his doubts about his mother's wellbeing.

"About as good as can be expected, Mum is hardly home with work and I'm just going through the motions myself, earning as much as I can to help while looking for a better job. A lot of my pay goes into the bills, I hardly have any left over after a long week. You?"

"Oh, you know, same old," she said cheerily. "The uni life is full of study and people trying to make you party instead of attend lectures. It's a fun yet tiring balancing act." As she said it a pair of rather cute students walked past the table, catching Mike's eye.

"Hmm, maybe one day I'll wise up and join you in academia."

"Yeah, you'll fit right in with the social party scene, until you fail your first semester!" Lily took a long sip from her drink, smiling over the rim of her cup. "Sooooo, on the topic of socialising, are there any girls in your life that I should know about?" she teased. Mike smiled, and made a decision on the spot that in the end would change him forever.