[M]y [F]irst time at her homemade glory hole

Back in the Craigslist personals day I stumbled on an ad that would lead to one of my favorite naughty stories. As many know, the now extinct personals held the opportunity for anonymous, discreet adventures. In reality, they were filled with spam and scams, especially in the women seeking men ad section. However, I was a young, 19, with too much time not to explore the pages. and too horny not to try to see I could land an adventure.

The ad that caught my eye was short on details, and felt like another scam. 

— Local GH open, looking for hung young men to drain. Send pic, stats, and location. 

Not thinking much of it, I sent over the required details, including a fun pic that made me look as hung as possible.

Later that afternoon, to my surprise, I received a short email. Love your cock, message me, throwawayk!k. 

Hastily, I downloaded the app and shot off a response.

“got your email, glad you liked how it looked. i think you’ll like how it tastes”

2 minutes later:

“mmmm i think so too, i love the taste of cum”

For the next day and a half me and this anonymous host swapped the filthiest messages that had me walking around with a hard on that I struggled to keep tucked away in my pants. She promised to bathe my balls with her tongue, swallow every inch of my cock down her throat until her nose was pressed against my body, and to slurp up every drop of my load. In turn I told her I would fuck her throat like it was my personal sex toy, save up my load until i saw her so i could cover every inch of her, and leave her gasping and cum drunk, a fulfilled cockslut. 

Finally the day came. She gave me a time and location. 1030am, at this cross street. She was going to be sucking off multiple guys, so this was a way to make sure we didn’t run into anyone and so her neighbors didn’t think something fishy was happening. When I got there I was to message that I was in the area. I would then be sent another message with more instructions.
 
In fear of missing my time slot I got to her neighborhood 15 minutes early and spent the extra minutes walking around, constantly refreshing my phone to make sure I didn’t miss anything, with my thoughts racing. What if it was a sick prank and I ended up knocking on some unsuspecting person’s door? I had already decided that I was ok with the likely scenario that it might be a guy behind the curtain (a blowjob was a blowjob). 

At 10:28, I sent a message that I was in the area, at the cross street. At 10:33 I got a message in return.

“1234 Main St, let me know when you get there and I will unlock the door, don’t knock. Wait 15 seconds to come in and lock the door behind you, and then walk down the steps to the basement, in the back there is a curtain. No funny business, my boyfriend will make you leave if you break any rules”

Reading the message sent another wave of butterflies through me. It was happening! I walked the block and a half over and sent a message that I was here. 30 seconds later I heard the faint sounds of footsteps walking to the door, the sound of the deadbolt sliding open, and the door relaxing open, slightly ajar. I then heard those same footsteps run away as I started the 15 second countdown in my head. 

Upon reaching 0, I pushed the door open and closed it behind me. To the right I could see the set of stairs leading to the basement. The steps down were dark and there was the unmistakeable sound of two people having sex. As my eyes adjusted, I followed the sound to the back of the basement where I saw a sheet with a hole in it. 

Reaching down into my pants, I pulled out my quickly swelling cock and slipped it through the curtain. Immediately, I felt a smooth pair of hands wrap its fingers around me, causing me to gasp. They slowly massaged my balls and stroked my cock, pulling me further into the curtain. Then I felt the hot, wet sensation of someone’s mouth enveloping my cockhead as her softs hands continued to massage my balls. I had had good blowjobs before, but I could tell this one was going to be my best by a long way.
 
Slowly she worked her mouth up and down my member, hands now resting on my thighs as I got harder and closer to full mast. She would alternate between doing this and sucking my balls one at a time, while slapping my fully engorged cock against her cheeks. After taking my cock in her mouth again she began sucking me down inch by inch until I reached the back of her mouth. She then reached her hands up to my hips and pulled my cock down further, pushing it down into her throat, her nose pressed against my pelvis, throat gagging on my cock. Here, I remembered her mentioning that she wanted me to use her throat like a fleshlight and began really thrusting my hips, slipping it in and out of her throat. In turn, I could feel her boyfriend fucking her from behind, forcing my cock into her throat. She was stuck between two hard places.

Quickly, the sounds of her gagging, and the sensation of her moaning on my cock as her boyfriend fucked her became too much, and I felt the familiar feeling of my loins tightening. Through the curtain she must have been able to hear my breathing increase and my thrusting become more erratic, since she immediately increased the intensity of her work. Gagging became louder, I could feel her spit and saliva lubing my cock, and her hand reached up again to softly caress my balls. This proved to be the tipping point and I felt my cock explode as she took my shaft out of her throat and began jacking me off onto her tongue. After cumming for what felt like forever, I heard her swallow and felt her soft tongue again cleaning my cock.

After my cock was clean enough for her liking, she tapped my cock head lightly, and I slipped out of her gloryhole, zipped up my pants, and walked back up into the light of the morning. 

As I walked away from her house my phone buzzed with a notification. 

“That was yummy stud, come back again”

I definitely did return, many times over the following couple of years, for more fun than just oral. Although I haven’t returned to her hole in a while — school, covid, and scheduling, I feel tempted after writing this story to open up the app again and send a message to see if her holes are still open.

Source: reddit.com/r/gonewildstories/comments/snas9a/my_first_time_at_her_homemade_glory_hole