Jeans Unplanned Gloryhole Train

Jean had known I frequented gloryholes before We became a couple. She continued to support my 'addiction' within Our relationship. We were both BiSexual and often played with others together and separately.

"I want You to fuck me through a gloryhole, Jean announced halfway through desert one Friday night.

Both excitement and surprise stopped me mid-chew. Our eyes met and I knew She was serious.

"I've given it alot of thought." She continued as I resumed chewing. "You've supported all my wilder fantasies and desires, not to mention participated in activities outside of Your comfort level. Though You enjoy most even today."

She paused. We both studied each other for a few minutes.

"OKAY!" It was Timmy, at work. She finally spoke up. "You know, the cute, young, Gay Guy I work with."

I smiled because I knew where this was going.

"Exactly." Jean pointed at me and smiled. "He told me what happened last weekend. He said He was feeling guilty having been fucked by my Man."

I took another bite and listened.

"I told Him that I knew what my Man was into, and that I supported it." Jeans smile got mischievous. "I have to admit, by the way He described Your fucking through that gloryhole...I was a little jealous!"

"So when are We doing this?" I asked before taking the last bite of my desert.

"Tomorrow afternoon. Early." Jean said confidently.

"Sounds good." I said with a smile as I got up and began clearing the table.

------------------------------------------------------------------------------------------------------------------

Morning came. Final preparations were made for Jeans first visit to my weekly 'stomping grounds'.

Jean dressed in a tight, white tank-top that was partially see-thru. No bra. A mid-thigh denim skirt and no panties. Her dark auburn hair down, which was just past Her shoulders. Her cute little nipples were as hard as ever from Her excitement.

I wore a denim button-up shirt and my usual cargo pants with no underwear. I packed a few 'accessories' for the visit to surprise Jean with.

"I'm so excited I'm soaked already!" Jean whispered as I parked in the ABS lot.

She reached under Her skirt and pulled out a soaked hand.

Licking Her fingers clean and kissing Her palm, "I sure like it when You're ready to go!"

Concern was added to Her excitement when She noticed all the vehicles in the parking lot. "Is it always this busy?" She asked.

It took me a few minutes before I remembered... "The first Saturday of the odd months was 'Couples Only' day." I informed Her. "That's today."

"...oh..." was all She could muster.

"We can come back next week, If You want to wait." I offered.

"I'm WAY to horny to wait!" Jean exclaimed as She opened the car door. "Let's go!"

I hurried to catch up. We entered and I pied our 'fee'. I led Jean into the booth area. All of the 'couples' booths were closed and some that I knew had gloryholes. The 2 booths that I wanted were still open. One was a corner booth consequently only had one gloryhole. That would be Jeans booth. I went into the 2nd booth and set up a couple of my wireless cameras. I left and closed the door to make it appear occupied. Jean and I went into Her booth and I began prepping Her.

I I strapped Her hands to Her knees. Lifting Her skirt, I backed Her bare holes up to the gloryhole. I tied a rope to the handle well above the gloryhole and fastened it to Her favorite choking collar. Now She could not get away from the hole, AND could choke Herself as She desired. I placed a notepad on the supply bag on the bench in front of Her with the app open to the cameras in the other booth. I then began setting up the other wireless cameras so I could watch Her.

"Scott?" Jeans voice rang with desperation.

Before I could respond, I noticed movement through a gap between Jeans ass and the top of the gloryhole. I looked at the notepad and saw a Woman and Man were in the next booth. The Woman reached out and caressed Jeans soaking pussy.

"OOH...She is so hot and ready. I heard the Woman exclaim. Jean and I watched as She got on Her knees and began licking Her pussy. Jean instantly began panting. One of the cameras showed Us the Woman had Her face deep into Jeans playground and was going at it! It only took a few minutes before Jean started to orgasm.

"Do You want me to stop them?" I asked

"Fuck no!" Jean exclaimed as quietly as possible as another orgasm hit Her.

Jean leaned into the collar, adding to the next orgasm. I pulled Her tits from the tank-top and pulled 2 weighted nipple-clamps from the bag. I was gonna save them for later, but now was as good of a time as any.

Jean again leaned into the collar, hard. I noticed the Woman had stood. The man now had His cock buried deep in Jeans pussy and was pumping long and slow. I pulled another strap from the bag and ran it between the handles on either side of the gloryhole. Her hips were now pressed hard against the hole giving the strange man even more available depth.

10 minutes of this strange Man pounding my Womans pussy was all it took for Him to erupt deep into Her with a deep powerful groan. Another Man stepped up as the first stepped away. Without hesitation, slammed balls deep into Jeans cum-filled pussy and pumped hard and fast. It only took Him a few minutes before adding His cum to the first load. Another Man stepped up. A very well hung black Man.

I bent down to whisper in Jeans ear. "Look at the screen. You're about to have one of Your fantasies fulfilled."

Jeans eyes widened at the sight of the massive black cock, and then at the feeling of it spreading Her pussy to new widths. He was slow and gentle. His 10-12inch long and over 2inch thick cock worked deeper into Jean every few pumps. It took a few minutes, and orgasms, before He was balls deep. Long slow strokes of His cock had Jean orgasming with almost every thrust. Slowly over the 15minutes Jeans pussy was being destroyed, He increased His pace. Towards the end, He was holding onto the handles and pile-driving so hard and deep into Jeans poor pussy, I thought He was going to break down the wall that was between them. When He finally came, He came so powerfully that He and Jean were grunting at the same time with each rope He shot.

He rested deep inside my Woman for a few minutes. After withdrawing, a Young Woman knelt down and lapped up as much as possible of the massive amount of cum pouring from Jeans pussy. Jean was in a state of constant orgasm, Another Woman knelt down to help. They took turns slurping up the cum and fingering both Jeans holes.

A 4th Man stepped up as The Women stood. "I want Her ass." He stated as more of a request.

I drizzled some lube down Her ass crack. Seeing it, He began working His cock in small circles around Her puckered asshole. Pressing in, Her asshole swallowed His cock. Jean groaned as the Man began pounding away. Jean leaned into the collar harder than ever. Her body convulsed time and time again as the assgasms raced through Her body.

I had pulled my cock out and was stroking it inches from Her face. Knowing I was close, I slammed into Jeans mouth. Within moments She was gulping down my cum. A minute later, a load of cum was shot into Her ass.

A 5th Man stepped up and slammed into Jeans ass. It was only a minute before He came. He was gone as fast.

The 6th Man I recognized as a neighbor of Ours that would webcam with Jean a few nights a week. They would masturbate together for an hour or so.

"Jean, it's Adam!" I whispered. "Now You get to feel it as You watch it."

I wanted to leave the booth She was in, not having thought how I was going to keep it latched. To protect Her privacy, since She worked with the public ALOT. I put a mask on Her face. She could still watch the webcams, but Her mouth was accessable.

I slipped from the booth and saw a dozen Men and Women outside the booth where they were having their way with Jean. As I got to the door, Adam walked out and turned in my direction. He stopped when He saw me. We gave a knuckle-bump and He walked past.

I peaked in the booth. A young-looking and fit Man was pounding away at one of Jeans holes.

2 more men and 2 Women had Their way with one or both of Jeans holes before I had my turn. Both Her holes were cover in cum, swollen, and red. I licked Her pussy clean, much to the appreciation of the onlooking Women. I had never felt Jeans pussy so hot and abused. It still felt wonderful around my cock. I pulled my phone from my pocked and opened the app for the cameras in Her booth. There 2 Men had their cocks in Her face. She was alternating sucking one, then the other. there looked to be a few loads of cum on Her back and many in Her hair. I changed cameras and was watching my cock sliding in and out of Her pussy. Switching again was a closeup of Her face. It looked like many had already cum on what little of Her face could be seen. As a man began facefucking Her, I decided to take Jeans ass.

15minutes in Her pussy and another 10 in Her ass was all I could handle. I added my cum to the countless others She had received in all 3 holes, not to mention in Her hair and on Her back.

The crowd had thinned out alot by the time I got back to the booth Jean was in. I managed to keep anyone else from coming in as the 3 in there each finished off...2 in Her mouth and one on Her back.

They were still pounding Her pussy and ass when i began to unstrap Her. I unhooking the collar. Undoing Her hands from Her knees, She was still being fucked in the ass. She held onto the strap from the upper handle until He finished.

Before I could unstrap Her hips releasing Her from the hole, Jean told me to wait.

Motioning to the notepad still showing the other booth. The well-hung black Man was back.

"Take my ass!" Jean exclaimed loudly.

The man obliged. Jean instantly regretted it. Though Her asshole had been abused by many, including myself. She wasn't prepared for the destruction She was now receiving from the massive black cock! Her wailing, moaning, and groans were echoing through the booth area, and likely the whole ABS.

Jean was ass-gasming from the most pleasurable pain she could imagine! The relentless pounding Her asshole was receiving had the weights on the nipple-clamps flailing in every direction. Yanking and jerking Her nipples in ways I was beginning to be concerned.

Finally with thrusts that I thought would dislodge the wall, and Jeans bowels, He came harder than I've ever seen or heard.

I unstrapped Jeans hips, but She couldn't move. Her ass was still impaled on the massive black cock that continued to blast cum into Her.

After nearly 5 minutes, the giant cock fell from Her ass, along with what looked like a pint of cum.

I gathered up the cameras. Not having expected things to go the way they had, Jean had to wear Her cum-soaked tanktop and skirt. The top now clearly showing Her dark areolas and unclamped nipples poking. The intense soreness made walking difficult for Jean. Adam happened to be there and assisted me in getting Her to my car. I was approached by a few Woman and a couple Men. We talked briefly and I was given some business cards...a couple Lawyers, a councilwoman, an accountant, and a doctor. I gave them each one of Our cards and We left.

Every movement of the car on the way home was causing jean to orgasm. At home, I placed jean into Our hot-tub out back so She could finally relax.

Adam came over and visited with me. We talked about what Our intention was for the night. He was happy it went 'off-the-rails' as He put it.