The Dangers of Glory Hole Dating

"Actually, there is someone – I wouldn't call her a girlfriend, but, well, I don't know." He shrugged casually. "What we have works for now." Lily tilted her head, analysing him.

"So your answer is: a girlfriend, sort of?"

"Something like that."

"Wow, glowing report. Utterly thrilling. I'm captivated by your fascinating lifestyle and yearn to know more." Mike slapped Lily on the head with his napkin and took a sip of his own drink as she giggled to herself.

"Do you guys talk much?" she asked.

"Not really...actually there's a lot about her I don't know still."

"But you are interested in her. Otherwise you wouldn't be bringing it up, right?"

"Well...I have been thinking about her a lot lately."

"And when you think about her, you want to talk to her, and get to know her better?"

"Definitely." Lily smiled wider, smacking his arm lightly.

"There you go! Sounds like you're pretty interested to me."

"Yeah, yeah I guess I am." Mike said, nodding to himself. He'd tried not to think about Jessie that way, because he was afraid she wasn't into him in the same way as he was into her. Admitting he had feelings for her felt really good though.

"So where did you meet her?" Lily asked, sipping on her tea.

"Well, we started talking online a while ago," Mike said, trying to think of a way of telling the truth while omitting certain elements from his story. "She's a student, I think, introduced me to this great place to hang out. We've been there about four or five times now."

"Oh? What is it, a coffee shop or something?"

"Well, no, it's a bar, fairly colourful place. We meet there on Thursday usually, kind of a regular thing."

"Oooh, nice. Where is this colourful place?"

"Actually it's that historic joint up north, the only one open until early in the morning..." Mike trailed off as he noticed Lily staring at him.

"You've been going to Swinging Jacks? Wait, you're meeting a girl there??" Mike suddenly felt uncomfortable. The corridor with glory holes wasn't very heavily trafficked but people must know it exists. Lily was good at reading people, and Mike's semi-guilty conscience started to get the better of him.

"Well, sort of, I mean we do meet there."

"And yet you hardly know the girl." Lily's mouth dropped open. "Oh my GOD, Michael – don't tell me you've been going out the back!" Now he started to feel indignant.

"I didn't say that! But, even if I do...well, so what if I have?? I'm a mature adult and I can decide what's right for me. How do you know about it anyway?"

"I – I work there!!"

"Oh of course, and yet I haven't seen you behind the bar or anywhere else despite me going plenty of times."

"You've been plenty??? Well, that's because..." Lily blushed. "Look Mike, I'm going to tell you this just once: Do NOT go back there again! It's better if you just forget about – that area – and whatever you're doing there. Seriously, I know the place and the people who go there and..." she hushed up suddenly, and Mike turned to see a flash of blue skirt and a wave of golden hair as his sister Grace hugged him.

"Hey guys!" Grace said perkily, releasing Mike and sitting down next to Lily. She noticed the strain between the two and looked from one to the other. "Is everything ok?"

"We're fine," said Lily quietly. "Mike just needed help with something." Grace smiled and for the rest of lunch Lily acted like nothing was the matter, but every time Grace turned away she looked at Mike with a livid expression, and he could tell something was seriously wrong with her. When she got up to go to the bathroom Mike turned his attention to Grace.

"Does Lily have a boyfriend?" he asked. Grace smiled.

"Cousins don't date cousins, Mike, no matter how good looking they are," she said giggling. "No, I don't think she does, which is a surprise isn't it? I mean she's always been gorgeous and she's even trimmed down lately. Something about a diet I think, I don't know how she does it but it's making me jealous. Why do you ask?"

"I dunno, guess I thought maybe she did or something. She seemed...odd. I was just wondering if she had met someone but didn't want to be seen with them or something." Grace gave Mike a puzzled look.

"Lily? I don't think so, come on Mike you know that's not like her." She thought for a moment. "No, I'm pretty sure Lily would have told me, or I would have figured it out myself. We hang out all the time and go to the same parties, and I never see her with anyone." Mike looked into her green eyes, wondering if Grace was covering for Lily, but she seemed genuine. They finished up as Lily came back and for the rest of the lunch things went like normal. Mike told them both about things at home and they shared stories of uni life, all the "networking" they were doing, and how it felt living out of home.

When their catch up was over Grace gave Mike a hug.

"Give one to Mum too...and please take care of yourself. I don't see you nearly enough and I miss you!" She turned to go and Lily whispered in his ear.

"Swinging Jack's isn't a place for you," she said furiously. "I don't want to hear that you've been back there, and I'll know, ok?" She put a smile on her face and followed Grace off into uni, leaving Mike to guess what she meant by that.

Perhaps Swinging Jack's is a haunt for uni chicks? Mike guessed that was how Lily knew about it. She was in the third year of her degree; one way or another she had to know at least ONE person who was involved in a hook-up club. University isn't all like the movies, but at the same time people had to get that impression from somewhere. Either way, he wasn't going to stop emailing Jessie anytime soon.

–-

As it turned out, Mike didn't actually have a choice. Firstly because he got several job interviews in a row on top of work, and his mother put her car in the shop to for repairs so he spent a lot of time helping her drive around town. When he did finally get a chance to spare some time for his mystery girl two weeks later Mike was taken by surprise: instead of him getting in contact with Jessie, it was she who emailed him first.

Mike stared at the email on his screen, reading and re-reading it over and over.

To: "james"

Subject: RE bj reward

hey, sorry its been a while, i had to do some thinking, but...ive actually just been thinking about u. funny, rite? i cant help it, was wondering if u wanted to meet up again...are u still interested?

hope to hear back soon,

Jessie xx

Whatever had bothered Jessie last time they met up had obviously been serious, but now she was the one asking to see him. He was definitely keen, and sent her a quick reply.

To: kymhy

Subject: RE bj reward

thats ok, ive been busy too. glad to hear from you though.

i could see you later tonight, if youre free? ill be available in about an hour or two, lets say the usual place at 8 :)

As he showered and got ready to go see Jessie, Mike considered her email. While he didn't mind paying to see her, he wondered if she wanted to meet up because she was expecting the same amount as after his poker night. She didn't seem greedy and surely she realised that was a special case, but it still nibbled away at him.

When Mike arrived the place was lively and he had a little trouble squeezing through to the back. As he got to the corridor he heard a door close and saw the light above booth 3 coming on, meaning he had just missed Jessie going inside. Feeling a tad disappointed that he missed a chance to sneak a peek at her, Mike quickly got into booth 4 before someone else decided to occupy it, and tapped the wall.

"Hey! Umm just hang on." Jessie's voice echoed from the other booth, distorted by the wall between them. He heard a muffled sound of her moving around and waited patiently for her.

"Sorry, I've just got a lot going on at the moment." Mike heard her sit down and smiled.

"It's alright, no need to apologise, I'm right here."

"Cool." Silence. "I'm glad you came. I know I kind of freaked out last time."

"No you didn't...it was fine, really. I enjoyed last time."

"Me too." More silence, and Mike started to wonder what was going on in her head.

"Did I feel good?" she asked eventually.

"Yes, you did. Smooth, wet, hot...perfect," he replied.

"Give me your hand," she said through the wall. Mike obligingly leaned down and reached through the hole, feeling her hand take his. Before he had time to ask he noticed the brush of fabric as his hand was brought up underneath a skirt and Mike felt the soft, warm wetness of her pussy on his palm. Feeling slightly surprised, he held still as Jessie gently moved her hips back and forth, grinding against his hand.

"I need this," she moaned through the hole. Mike rubbed her softly, his fingers getting wet as they slipped over her folds. Slowly he moved his hand higher up so that his palm was pressing down on her clit as his fingers gently pushed inside her. Jessie moaned again, louder this time, her slender hand gripping his wrist as he fingered her. Back and forth Mike moved his fingers in her pussy as Jessie rocked her hips to rub her clit, her breath coming in shallow gasps.

"Make me cum," she panted. "Fuck me with those fingers!" Mike thrust into her deeper, receiving a startled cry of pleasure as Jessie's legs quivered. Then Mike had an idea and slid his fingers out of her pussy. Jessie groaned.

"Why'd you stop?" she asked, breathless.

"Come closer," mike whispered back. He knelt down and saw Jessie's naked pelvis, gazing upon her soaking wet pussy and her smooth, milky thighs, her skirt hiked up around her waist and a pair of panties down around her knees. She was clean shaven, and her folds were pink and red, gently flexing as she squirmed with anticipation. Mike licked his fingers.

"Mmm...taste's good," he murmured. "I'd like some more, please." He watched her shuffle closer until she was almost at the hole, standing close enough for him to smell her scent. Jessie seemed nervous so Mike encouraged her.

"Press yourself against the wall," he instructed. He felt a quiet bump as Jessie's upper body touched the wall and her pussy reached the hole. Leaning in close, Mike flicked his tongue out over her clit, making Jessie jump and gasp. Smiling to himself, Mike took a longer lick up through her folds and back down again, the tip of his tongue moving rapidly as he slid it into her. Jessie was beginning to shake again so he quickly pushed it in deeper, tasting her juices as he fucked her entrance with his tongue.

"Mmmmm," he moaned. Jessie whimpered and pushed her hips as far forward as she could, her lips pressing against Mike's as he licked and played with her pussy. His fingers moved up to slide inside her again and his tongue found her clit, sucking on it and flicking across it as he inched his fingers in and out of her. Jessie was moaning and shaking hard now, her legs quivering underneath her, struggling to hold her up.

"Fuck me," she breathed. "James, I think I – I'm going to cum! Ohhhh...!" Jessie's juices sprayed gently across Mike's face as he licked her folds once more, running his fingers from her pussy down the stretch of skin to her ass and back, his tongue buried deep inside her. He licked and sucked on her folds harder as she came, riding a wild orgasm in the booth next to his.

When she had finally stopped gasping for air and twitching at every movement of his, Mike slid his fingers back through the hole and stood up, wanting to look though and see more of her but not wanting to steal her privacy. He heard Jessie collapse onto a chair in the booth, her legs still shivering.

"Woah, oh my fucking GOD," she gasped, panting for air. "I don't think I've ever cum so quickly." Mike smiled, leaning closer to the hole.

"I could do more...if you turn around." Mike heard Jessie fumble on her chair, wondering what she was doing.

"No," she said quietly. "No, I can't do that." Mike heard her moving articles of clothing and worried she might be leaving.

"Wait, Jessie I didn't mean, sex," he said, fearing she had misinterpreted.

"It doesn't matter, I can't –"

"Hang on, I'm sorry, we got started so quickly I forgot." Mike slid the money through the hole, hearing it fall to the floor. Jessie didn't reply but Mike heard a quiet sob from the other room.

"It's not about that. It's not about the money at all." She sounded upset, and Mike felt terrible. He wanted to comfort her, to bust down the wall and hold her.

"What is it, then?" he asked timidly. "I don't want to lose you."

"That's just it!" she wailed, the sound echoing oddly in the bare wooden booth. "There's nothing to lose! We aren't supposed to get attached! I know I shouldn't be doing this I just, oh I don't know!" She sobbed and Mike reeled. Attached?

"I just meant...look, Jessie, do you like what we do?" There was silence for a minute.

"Yes," she whispered sadly. "I wanted you to come to me this time."

"And do you like meeting like this?"

"Yes. No. Wait, not with the money. It isn't about the money – not with you."

"Well," said Mike, taking a gamble. "Why can't we just enjoy ourselves then? The rules haven't changed." Jessie gulped again, her breath quietening as she seemed to calm down. He heard a shuffling on the other side of the wall.

"Come here," she said, her voice coming from right next to the hole. Mike shuffled closer, wanting to look in, but instead her hand came through the hole and waited for him. Mike stood up and unzipped his pants, gently placing his cock in her small, soft hand. Jessie gave him a few rubs until he was rock hard, gently moaning on the other side of the glory hole. Mike watched her fingers slide up and down him, caressing his shaft as he got bigger. There was something very sexy about those fingers, and slightly kinky seeing just a hand sticking through a hole to give him a handjob.

"I love this," she said. "I love feeling it in my hand, it's just so...perfect, I guess. Like it fits so well, and I cant get enough of it. Sometimes I just want to swallow your cock as far as I can go, and it kills me that I have to wait for us to be here."

"As long as you want it you can have it." Jessie didn't reply, but Mike felt her tug insistently on his hard cock and he moved closer, feeding it through the hole and straight into her waiting mouth. She eased back, kissing the tip of his cock and letting it part her soft lips again, slower this time. She kept moving slowly until her mouth actually reached the base of his cock and she started to have trouble, pulling back and rubbing him with her hand. He still didn't have a condom on and her fingers around the head of his cock felt amazing.

Mike felt Jessie move around on the other side of the wall, her hand still grasping him tightly as she jerked him off.

"God I'm so horny over here," she moaned, her mouth sliding over his cock and sucking him harder. "I'm playing with myself, babe...that's how much your cock turns me on." Jessie deepthroated almost all the way down again and Mike heard her gag before pulling her lips back, her head bobbing faster as she blew him, one hand jerking him off at the base of his shaft. Mike felt a familiar sensation and leaned as far forward as he could, sticking as much of his cock through the hole for Jessie to play with as possible.

"Cum for me baby, I'm ready for it," she breathed, her hand jerking him even faster.

"Oh fuck I'm cumming babe," he moaned. Jessie placed her mouth over Mike's cock and gave him a long suck, pulling her head back as he tapped hard against the wall. She was just in time and he started cumming hard, his cock pumping in her fingers. Mike groaned loudly, listening to her muffled pants from the other side of the wall, still tasting her on his lips.

Jessie was shivering on the other side of the wall, Mike could feel it through her hand. She gently kissed and licked his cock as they both calmed down, stroking him slowly before letting him go completely.

"I have a surprise for you," she purred quietly. One of her hands returned to rub him, keeping him hard for a few seconds, then released him as he heard her moving on the other side of the wall.

"Thanks," she said happily. "I can't tell you how much I enjoyed tonight."

"Me too...so, are we ok?" Jessie didn't reply at first and Mike wondered if she was about to leave on him again. Then, to his relief, a positive reply.

"Yeah, I think we are...better than ok, maybe." Mike smiled and sat back on his chair. "I need to think about something though, so I'll contact you, ok?" The door on the other side scraped open to the sound of loud heels clicking up the hallway and Mike started doing up his pants, but then he heard the heels return and a noise on the other side of the wall. With a flutter, the money he had pushed through the hole popped back over to his side. He looked through the hole at a pair of long gorgeous legs and black heels.

"I didn't come here for the money," she said quietly. "I got something better." And with that she walked off.

Mike went out to his car and climbed in, accessing his email on his phone and finding a new message from Jessie, this time with an attachment. He opened it and saw a picture of a near-perfect set of tits, pink and fleshy, the nipples standing hard as a small hand with sexy fingers teased one of the nipples. They were framed by a white button up blouse, opened at the top and closed just underneath her breasts, as if to hold her gorgeous globes up. The caption read "these should be yours".

The next photo was the same sort of shot, except this time there was a cock in the picture, her red nailed fingers wrapped around it, and hot, white cum had sprayed all over her tits. One strand went from the gentle curve of her neck, just visible at the top, all the way down to her nipple, a bit of it just about to drip off the end. Her hair must have been very short or tied up because he couldn't see any of it, but the sexy curve of her bare neck was enough to drive him wild. This one had a caption too:

"you got some on my cheek as well. cant wait to do that again".

Mike's cock got hard instantly and he stared at those beautiful breasts for ages, mesmerised, wanting desperately to feel them in his hands, to play with them as she was playing with them, until she sucked him off again and he got to fulfil her wish and cum on them once more.

–-

Mike went a week without hearing from Jessie the mystery girl. In that time he reflected on how he was beginning to feel about her. He knew he was getting attached, but was it to the sex or the girl? And what did that even entail? With each meeting he learned more about her personality, her dreams, things you would tell people you were in a relationship with, yet he still knew next to nothing about her on the outside. Jessie had mastered the art of telling him about herself while leaving out the things that would reveal who she actually was, like where she worked, what she looked like, her friends and social life...when Mike stood back and considered it, he probably couldn't pick her out on a dating website if he tried based on the things one usually puts up.

Despite all the secrecy, he still felt drawn to her like no one else before, drawn to the intimacy of her answers, to the things she had expressed to him. It was the weirdest feeling, to learn all the important parts of someone's life without knowing the basics first. It was like being thrown into calculus before learning addition.

Eventually Jessie messaged Mike again, and he felt himself bursting with excitement.

To: "james"

Subject: RE bj reward

Hey, sorry for the long wait. i kno i usually message you more but i had 2 think.