The Dangers of Glory Hole Dating

honestly...i dont talk to ppl as much as i do 2 u, and not about the same stuff. i feel like i can trust u, like maybe...i dont kno, maybe theres something different about u. i kno there is...and i think uve felt it too, right?

Mike thought long and hard about his answer, wanting to get this first response right. Eventually, he typed out something simple and sent it off with baited breath.

To: "jessie"

Subject: RE tonite

hey, im glad you messaged me, i was beginning to think you had changed your mind.

its definitely odd, our relationship. i cant think of any other way to describe it. but odd isnt a bad thing. in fact, i think its good. very good. so good that it might be the best relationship ive had in a long time.

ive been doing thinking too. ive been thinking i dont know how i feel about you, or maybe what im supposed to be feeling, but i know how i do feel...I like you, Jessie, and i like what we do together, and i dont want to stop anytime soon.

if you feel the same, i want to keep talking...and who knows what else.

James

Mike waited patiently for his reply, knowing he had decided to take things forward and feeling nervous. Everyone was looking for that special someone – could he have found her?

To: "james"

Subject: RE bj reward

thats exactly how i feel! i dont kno when we shuld move forward but maybe we can get to kno each other better...especially if we meet up again ;) wat do u say?

i dont care how we met...all i care about is how i feel

Jessie xx

Mike smiled wide. They chatted back and forth for a little while, learning things slowly but surely, still keeping their real lives separate. Mike knew in time that would come around, and he would tell her all about his problems at home with his mother and his work, but he was starting to feel like it didn't matter so much. He knew Jessie, the real Jessie, who she was on the inside, and he was slowly but surely falling in love with her.

–-

A few days later Mike was waiting to hear from Jessie again, but unfortunately she had things coming up that kept her busy and unable to meet. The photo she sent him had been adequate for a while, but now he wanted to repay her properly. Her last message asked him to keep checking emails in case she got a free moment, and she hoped to have one soon, so he was patient.

Mike's mother on the other hand was starting to crack under the pressure. Lindsay came home one night looking completely worn down after starting early, working 10 hours and then having to take part in a work function. Mike understood all too well that when you were already exhausted and stressed out, having drinks with your boss who seemed to be taking it easy was the last thing on your mind. When she came in the door Mike knew it was time she had a break.

"Hello, dear," Lindsay said tiredly. Mike watched her walk into the lounge room and collapse on the sofa, half asleep already. Grace had sent him a message about organising a vacation for her recently and looking at her now, Mike felt she definitely deserved it, so he quietly slid a plate of food in front of her and ducked off to his room to look into prices.

It would have to be low cost, he reasoned. They had just managed to get on top of all their finances and the last thing they needed was more debt. But at the same time, the way they were both working their asses off, he knew they could probably afford something decent. It just didn't have to be anything too crazy. Mike knew when she got back she would start working her ass off again, but she would feel ten times better than she did now.

As he typed away, a message from his email popped up in the background. It was Jessie. Mike quickly changed windows and opened it up, eager to see what she wanted.

To: "james"

Subject: RE bj reward

hey big boy ;P i know i shouldnt be doing this, im tired and ive already had drinks this evening, but im super horny and i need u bad. i just need a release. i kno we started out not wanting to get attached, but ive been doing so much thinking about u and at this point i dont know why im not fucking u yet, u already know i want to!!

only thing is im right on the limit so i don't know if i can drive, but...r u free tonite? i know its late notice but i promise if ur free ill make it worth the effort ;)

Jessie xxx

Mike started to reply but paused. His mother was alone. She needed him and he didn't want to abandon her. With a sigh Mike got up and went to check on her.

Lindsay was still in the lounge, her shoes kicked off and her eyes half asleep. She looked up as he entered.

"Hey sweetie, how was your day?"

"I'm alright, Mum, but you look really tired." She sighed heavily.

"Yes, I know. Work wanted me to stay out later to meet some investors, but..." she dropped her eyes to the floor. "I told them I couldn't do it, that I had to stay home to deal with family things." Mike nodded and sat down on the chair next to her.

"Family things are important. Actually, it's a good time for it tonight. See Mum, Grace and I were thinking –" before Mike could finish his mother's phone beeped in her bag. He waited quietly, trying to be patient as his mother opened up her work messages. He couldn't stand waiting, Jessie needed an answer!

"More work?" he asked. She glanced up at him.

"They want me to send through some files, and at this time of night too..." she glanced over at Mike. "Sweetie, I know I haven't been around a lot lately and I need to talk to both you and Grace, but maybe tonight isn't the time. In the morning I'll tell work I was already in bed, which isn't too far from the truth since I really do need a good night's sleep."

"Ok Mum, if that's what you need I think you should go."

"Sorry sweetie, but if you want to go out don't let me stop you, ok? You won't wake me coming home or anything, and I think you need to spend some time outside." Mike nodded, staying while she typed out a response. When she was done she gave him a warm smile.

"Don't worry about me...you can stay out late if you like, I'm a big girl and can take care of myself." Mike kissed her on the cheek and took her empty plate away as she picked up her bag and climbed the stairs to her bedroom. Mike ran back to his laptop and quickly wrote out his reply.

To: "jessie"

Subject: RE tonite

hey, i am free tonight, my plans just changed. are you sure you can meet me? i really cant wait have some fun with you...

James

But Mike's heart sank when he read her reply.

To: "james"

Subject: RE tonite

i just checked, im over the limit :(

Damn it! After everything working out in his favour now Jessie couldn't drive out to meet him. Mike needed a plan, and he needed it fast. He typed away quickly, throwing in a little temptation on the side for her.

To: "jessie"

Subject: RE tonite

what about a cab? i could meet you at our usual place...and if you want, I think its time I fucked that sweet pussy of yours until the wall shakes and you cum all over my cock

Her reply didn't take long.

To: "james"

Subject: RE tonite

god id LOVE to fuck u too, i love our bjs dont get me wrong, its always fun to suck u but sex is a really big thing for me. i used to need it at least every second night, and id usually get it...one way or another ;) but its been ages for me.

and its not just that. i love ur cock so much, and i cant stop thinking about ur fingers ;D thing i definitely cant drive and i don't kno how much time wed have if i have to get a cab, it mite take a while, and i have somewhere to go later, so i dunno.

i am super horny tho...

He knew it! She wanted him badly! Mike had to think now. He didn't have much cash on him, but maybe sweetening the deal a little more would win her over, especially if she already had other plans tonight. Of course he didn't want their meeting to be about money, but if it was just one last time...who knows, maybe after tonight she'd want to meet properly? It was worth a shot. He quickly wrote back.

To: "jessie"

Subject: RE tonite

i want you too, im so keen for it.

look, it sounds like it might be awkward timing tonight, but, what if i made it worth your while again, just to help you out, you know? pay you back for the cab, and maybe a little extra...same place, same deal, and then maybe we can talk about what comes next? i think youll know what i mean...

James

In no time he had a reply, and this time when he read it his heart soared.

To: "james"

Subject: RE tonite

...just one last time? im insanely horny and i want to do this with u no matter wat, i really do...i need it to happen. but i dont want to be too late to this party, and it could cost a bit getting a taxi to the bar, thats all :( so if ur honestly ok with paying me again, just this once more i promise...then hell yes tonite we can fuck. god im so desperately ready for it!

we have to use a condom wen u finish though, cos i cant get my tits dirty tonight haha ;D

as for wat next...well, do u remember wen i said it wasnt about the money anymore? honestly, i said it becoz i feel like i dont want to take money off u for wat we do together...not wen its sooo hot! i almost want to pay u!

i dont know, ive been emotionally unstable lately and maybe this is all a bad idea and maybe im being silly and sentimental, but rite now i want u bad and cant wait to do this and...well, let me put it this way James, next time we have sex, we wont be using a gloryhole ;)

i just hope u can accept me for who i really am. im ready to take the risk. r u?

love,

Jessie xoxoxo

Oh. My. GOD. Mike sat staring at the email for a solid minute, reading and re-reading the words to let them sink in fully. She wanted him! She loved him! This was perfect!! Mike grabbed his towel and headed for the bathroom. He wanted to be clean and smelling his best when he won over his mystery girl!

–-

Mike was bursting with excitement as he pulled up in front of Swinging Jack's, which was crowded and bubbling with partygoers. He made his way through the group to the small corridor that was so familiar now and found to his dismay that their usual booth was taken. Casting around for another idea, he saw that booths 9 and 10 were both empty, so he dived in and shut the door quickly.

The booth had a gloryhole like the other one, but it was barely palm sized, so big enough for Mike to fit through, and maybe Jessie's hand, but much smaller than their usual. It also had a second hole up near his head, like a little peep hole, which gave him a bit of a view into the booth. He wondered if he should tell Jessie about it, but instead just messaged her where he was and vowed not to use the peephole too much...he wanted to see her, but also felt like he needed to respect her privacy a little.

After a few minutes he heard movement outside the door – heels, a girl's heels.

"God I'm already half-wasted," came a girly voice. "I can't believe I'm doing this...no no I'm fine, I can get in from here." Jessie was here.

"You sure you wanna do this tonight?" came another girl's voice, deeper and very unfamiliar.

"Yep!" Jessie said back. "I know what you're thinking, you don't approve either, but trust me this is the last time...I'll be ok, really."

"Alright then, I'll be out at the bar. Come get me when you're done and we can go."

"Hehe, see you soon Batgirl," Jessie giggled. A pair of heels walked away while a second set entered booth 10, shutting the door and locking it. Mike knelt down near the hole.

"Jessie?"

"James," came her soft reply. Mike smiled at the nervousness in her voice, feeling the same way. He reached out and poked his fingers through the hole and was suddenly met by her slender hand, fitting all the way through.

"Hey you," he said quietly. Mike held her hand and felt her fingers link with his, a strange and wonderful feeling. He kissed the back of her hand and heard her giggle.

"My gentleman! God I've really missed you."

"I'm here now. but...Batgirl?"

"Oh...hehehe, costume party. Guess who's Wonder Woman tonight?" Mike inwardly gasped at the thought of a Wonder Woman costume and all the things he would do with it.

"Gonna have to wear that another time." Jessie burst into a fit of giggles.

"I think I can do that. Now..." she said, releasing his hand and pulling hers back through the hole. "Come here."

Mike went to stand up but Jessie's voice stopped him as he began unzipping his pants.

"Wait, no...there's something I need to do, before we do this." Her voice was still coming from down next to the hole. "Kneel back down here." Mike slowly knelt next to the hole again, wondering what she wanted.

"Darn, I wish we had our regular booth. This hole is much smaller."

"Big enough though, right?" Mike asked.

"I wanted more, but yes, it will do," came her reply. "Put your mouth up to it." Mike leaned in, waiting to feel her wet pussy on his mouth, looking forward to sliding his tongue through her before getting down to business, but instead he felt a pair of soft, warm lips press to his. Realizing she was kissing him, he kissed her back, giving her as much romance as a glory hole could afford. Jessie's lips parted and after another half a minute of kissing her tongue slid through into his mouth. He returned the favour, wishing he could tear down the wall and get more of her. She tasted like heaven, soft and warm and perfect in every way. He was addicted to those lips the moment they met his.

Eventually Jessie pulled away, and Mike peeped through the hole to stare at a pair of ruby red lips, wet with the action of making out.

"Thankyou," she said, smiling. "I really wanted that...and I want more of it later. But we don't have a lot of time, so how about you stand up and give my mouth something else to do." Mike was desperate to oblige her, unzipping his pants and taking out his cock, already rock hard. He fed it into the hole and straight into her waiting mouth, feeling her open wide to swallow as much of it as she could. When she met her limit her head backed away from the hole so Mike could get all the way through, giving her his entire length to play with.

"Mmmm," she moaned with a mouthful of cock. Mike closed his eyes and leaned back, his hands flat against the wall as Jessie sucked him. He felt like he could go without sex for the rest of his life if he had these lips on him every single day! Her tongue danced around him as she did every trick in the book, running her lips up and down his shaft to wet him down before swallowing him as much as she could, backing off only to take his cock in one gentle hand and bob her mouth back and forth, slowly at first, then more and more rapidly.

Jessie's lips formed the perfect wet, warm hole for his cock, her hands running up and down him as though all she needed was to milk him dry, her hungry moans music to Mike's ears, muffled by the wall, the odd echo of the booth and his cock in her mouth. Any more of this and Mike would definitely cum, and he wasn't nearly finished with her, not yet.

"Oh my God, Jessie, I don't know how you got so good at that but I think I'm addicted to it." Jessie pulled back and giggled again, her hands never stopping.

"That makes two of us," she murmured. "I could put this cock in my mouth all day long and not get enough of it." She deepthroated again, her head bouncing as she made small, hungry gulping noises. Mike moaned loudly and tried to press his cock further into the hole, wanting everything she had. There was no way he was going to put up with a glory hole next time!

Suddenly Mike felt those soft sweet lips leave his cock, and out of curiosity he looked through the tiny peephole. His view wasn't great but he managed to see Jessie on her knees on the chair in the booth, her back turned towards him and her hands gripping the back of the chair. He could now see that she was dressed up in her Wonder Woman outfit and that she was relatively thin with long, jet black hair. As he watched she lifted her little blue skirt and raised her ass in front of the gloryhole, so he knelt down and gazed once again at her shaved little pussy. Her light pink folds were absolutely wet with anticipation. She was literally dripping over him!

Mike slid his finger through the hole and gently touched her pussy, hearing her moan as his fingertip slid up and down her folds. He eased it into her entrance and felt her shiver, backing up onto him and wiggling her bum. He eased back out of her and slid in again slowly, and instantly Jessie began making little moans. Mike slid his thumb down her folds and brushed it against her clit, feeling her clench and shiver around his fingers.

"Fuck I want more," she moaned, panting slightly. Mike twisted his fingers inside her and pushed a little deeper, his thumb circling over her clit faster in an attempt to please her as quickly as possible. He knew he would have no problems cumming tonight but he wanted to get her there before himself, to make sure she remembered this night.

"Mmm, damn you're tight babe," he whispered through to her.

"I-it's been a long time..."

"Too long, I think."

"I, ohhh fuck, I hope you know I get one hell of an appetite for sex..."

"Mmm, I can't wait to find out what else you're hungry for."

"I've never tried anal," she blurted out. Mike slowed down a little.

"Never?"

"Well, once, but it didn't really work so I don't know if it counts..." Mike slowly rubbed one of his fingers against Jessie's pussy, coating it in wetness, then pressed it against her asshole gently. Jessie froze, as if holding her breath, then she relaxed and Mike pushed against her, his finger easing into her hole.

"Aaahhhh..." Jessie panted, her body shivering slightly. Mike didn't push too far, easing his fingers back and forth in her ass and her pussy at the same time, feeling her tilt her hips and rock against him. Jessie was silent for a minute or two, just rocking against Mike's hand and slowly working herself backwards, his fingers slipping deeper inside her each time.

Mike heard Jessie fumble for something and a condom was pushed through the hole past his hand. trying not to let his fingers leave her pussy or her ass, Mike ripped the packet open and rolled the condom on with one hand, desperate for what was coming next. when he had it on he thrust his fingers in hard and pulled them out, giving some of them a lick. He loved the way Jessie's pussy tasted.

"Fuck me right now," she begged. "I just want it rough." Jessie pressed her cheeks hard against the hole, her pussy shivering and wet. Mike took the hint and stood up, wanting her as much as she wanted him. Slowly, he lined up to her folds and began feeding his cock through the hole and pressing it against her entrance, slowly pushing it into her. His eyes widened – she was so tight! As his chest touched the wall in front of him she clenched hard around him and Mike could tell he was deep inside her. A gasp came from next door.

"My God...I've wanted to feel this full for so long..."

Both of them closed their eyes at the feeling, holding still for a moment to let the memory of it sink in. Mike knew that no matter what happened, for as long as he lived he would never forget the feeling of his cock being completely buried in Jessie's pussy for the first time. He hoped someday she would tell him something similar.

"You're...a perfect fit," she moaned. "N-now take me, take my pussy, it's yours...all yours!" Mike needed no encouragement and started moving back and forth, thrusting in and out of her tight sweet little pussy. every time he pushed forward it felt like he wouldn't fit, and every time his shaft glided between her walls she gave him a gentle squeeze, milking his cock. It felt like heaven.