Aty at the Glory Hole

As most people seem to like knowing something about the participants in a story here is a little bit about us. I'm 40 years old, 6' tall, medium build, with long blond hair and blue eyes. Katy, the love of my life, is 38, 5'3" tall, with dark hair, gorgeous brown eyes, 34C boobs with nipples that protrude through about any shirt when they get hard, and a shaved pussy that seems to always be wet. I certainly have no complaints in the sex department as Katy is always ready to please me anytime and anywhere I'm "up" for it. We both have a strong sexual appetite and love to push each others limits from time to time.

We had a couple of free days without the kids and planned a trip to Boston for a bit of shopping and maybe some naughty fun. Katy wanted some new lingerie, which I never complain about, and it was time to add to the toy collection. I booked a hotel room, made dinner reservations and we headed to the city to see what we could get ourselves into.

As usual when we are taking a long trip, I printed off a few stories from literotica for Katy to read to me as I drove. She was wearing a mini-skirt and tight white T-Shirt for the drive. The T clearly exposed her arousal. As she read the stories, her long, hard nipples pressed hard against the cotton fabric as she absentmindedly rubbed her engorged clit and swollen lips as we drove.

I had purposely chosen stories relating to adult theaters to gauge her reaction as she'd never been to one and we'd only briefly discussed the idea previously. During the drive I was able to coax Katy into removing her T-Shirt and pulling her skirt up. She sat back in the seat reading and masturbating knowing full well any trucker that drove past us would get an eyeful. Katy has always gotten turned on when I show her off so this knowledge just made her hornier.

While admitting the stories made her horny as hell, Katy said she didn't think she could screw around with that many guys in such a seedy place but it was fun to think about. I just nodded in agreement and reminded her that I'd never ask her to do anything she wasn't comfortable with.

We arrived in Boston, checked into the hotel and jumped in the shower to get ready for dinner. Katy was stunning in a black miniskirt, shimmering and loose fitting black blouse, thigh high hose that just barely came up past the hem of the skirt, and a pair of heels. Under the gorgeous outfit she wore a pink lace bra and panty set she'd bought just before the trip. The bra had holes that allowed her nipples to poke through. I wrapped my arms around her and kissed her neck while rubbing her ass but she pushed me away saying I was going to mess up her makeup.

I had made reservations at an upscale romantic restaurant. As Katy stepped out of the car she allowed her skirt to ride up a bit, giving the valet a glimpse of her panties. I love for Katy to show off and she secretly loves to do it, though can conveniently claim she only does it because I like it. Our booth was at the back of the restaurant as I'd requested and was secluded enough that I could play under Katy's skirt while we waited for dinner. I whispered for Katy to undo a couple of buttons on her blouse, which she did, giving our waiter a direct view of her gorgeous bra covered tits and protruding nipples. The waiter stuttered through taking our order while trying to force himself not to stare down my wifes blouse.

After placing our order, I asked Katy to go to the restroom and remove her undergarments. She excused herself to do as asked then returned and tossed her panties on the table in front of me just as our waiter was stopping to check on our drink situation. Standing to let Katy back into the booth I grabbed the panties and shoved them in my pocket, apologizing to the waiter. As Katy sat down she was sure to bend over further than necessary allowing the waiter an unobstructed view of her now braless boobs. His hand shaking as he refilled our wine glasses the waiter asked if there was anything else he could do for us, Katy winked and said "maybe later". I knew the wine was having the desired effect on her with that comment.

During dinner I fingered Katy to orgasm, much to the delight of the waiter, bus boy, and manager who all suddenly decided to give us the best service ever. As we were leaving, Katy gave the Waiters crotch a little squeeze and a peck on the cheek as she thanked him for the wonderful service. I swear I think the young man came in his underwear right there.

We drove back to the hotel to drop the car off as neither Katy nor I will drive after too much to drink. We called a cab to take us somewhere we could go bar hopping. As the cabbie drove I opened Katy's blouse and sucked a nipple into my mouth. Afraid we were going to end up in an accident because the cab driver was too busy watching us in the rear view mirror to pay attention to the road Katy pushed me away and told me to behave while covering herself back up.

We spent the next couple of hours going from bar to bar having a drink and a dance or game of pool depending on the bar then heading on to the next one. The last bar was a dance club. We ordered drinks and sat down at a table to take in the atmosphere when a slow song come I. I asked Katy to dance so she slipped off her heels and followed me to the dance floor. With her arms around my neck I had one hand on her ass and the other on her tits occasionally lifting her skirt or pulling her blouse open to allow anyone who wanted, to get a good look.

After the song we sat down to finish our drinks. An attractive man in his late 20's asked Katy to dance as soon as the next slow song came on. She asked if I minded, to which I replied of course I didn't and to have fun. He took her to the middle of the dance floor where I could only barely see them around the other couples dancing. Returning to the table, she informed me that the fella had seen us dancing earlier and that emboldened him to put his hands under her skirt to fondle her ass as well. Not knowing what my reaction would be, she said she moved his hands up to her waist. She also said that he had felt up her tits and while they were dancing she felt his hard dick rubbing against her belly through his slacks.

Katy said she hoped I wasn't mad and that she tried to stop him. I asked if she enjoyed the stranger feeling her up. Instead of answering she took my hand and placed it on her bald pussy which was so soaked there was fluid starting to run down her leg. I took her by the hand and led her to the mens room where I unzipped my pants and asked her for a blow job. Katy is always up for sex in public, particularly after a few drinks, so she readily dropped to her knees and took me in her mouth never missing a beat while other patrons came in and out of the bathroom, trying to ignore what was going on. After swallowing every drop Katy stood up, kissed me, and asked "what's next?"

We hailed a cab and asked him to take us somewhere we could buy sex toys. The cabbie dropped us off an adult book store of sorts. A quick look around let me know there were also peep show booths and a theater in the building. Katy had never been to either so I was hoping to get her to at least check it out. As we walked in I pointed out to Katy that there was a theater in the back of the book store and reminded her of the stories she was reading to me on the drive in. I joked with her about going in and checking it out in a bit, half expecting her to shoot the idea down immediately. She just gave me a mischievous grin and said "maybe", while heading over to the toys section.

Katy was the only female in the main bookstore and realized she was obviously the center of attention as the same few men kept walking by gawking, trying to get a better look. Several times I asked her to bend over and grab something off the bottom shelf to look at. Being in a wine induced playful mood she gladly did as asked even shaking her ass and giggling as she bent over giving her admirers an unobstructed view of her ass. We bought a few toys and some lube, then I asked Katy if she wanted to go try them out. Quite eager, thinking I meant back at the hotel, she started walking toward the door to the parking lot. I took her hand and led her to the back of the store.

On one side of the building was the entrance to the peep booths, on the other side was the theater. Recalling her words from earlier that she wasn't so sure she'd want to play around so many horny men in a theater, I led her to the peep booths. Katy had never been to such a place before and held my hand tight as we made our way down the rows of individual booths. As with every other such place I've been, there were several men cruising around watching to see who was coming and going. Katy was a little uneasy about this until I told her I was sure the doors to the booths locked, which eased her fears some.

Checking the booths to find what I was looking for, I led Katy into one that looked relatively clean and had a love seat in the middle of it. Once the door was locked, Katy sat on the love seat and started opening the toys while I fed several tokens into the box and chose a scene of a woman taking on three guys at once, one dick in each hole. Katy was still worked up from dancing with the stranger and had a toy inserted before I even sat down. Dropping my pants around my ankles I sat down and took over moving the toy in and out of her pussy as she rubbed her very hard clit while intently watching the woman on screen take three cocks.

Breaking her trance when the scene changed, Katy took a quick look around the booth and suddenly slammed her legs closed on my hand. When I asked her what was wrong, she just pointed to the wall where there was a glory hole. Someone was looking through the hole watching me work the toy and it freaked her out. I calmed her down explaining that she'd read a story about them on the drive up and that they were for people to watch each other or enjoy anonymous sex through the hole, she just said she didn't realize they really existed and wanted to take a closer look.

I asked the guy in the next booth if he'd step to the middle of his booth so my wife could get a look at him. He did as I asked and Katy got on her knees to look through. She said the guy was standing with his pants and underwear around his ankles and that he was masturbating. I asked if she wanted to see his dick up close to which she gave a sheepish smile and just nodded. I instructed her in the universal glory hole signal of running a finger around the bottom of the hole and a long slender dick entered our booth within seconds, nearly poking her in the nose.

Eyeballing the cock sticking through the wall Katy asked "What now?". I asked "do you want to play with it?". Katy shocked me by saying "only if you do it first". She'd never before suggested anything of the sort during our fantasy talks but it wasn't unusual for either one of us to challenge the other to do something sexually, although this one was on a whole other level than previous dares.

Being drunk enough, horny enough, and not wanting to back down from any sexual challenge coming from Katy it was my turn to shock her as I asked her to hand me her bag. Taking out the lube we'd just purchased I poured a bit of it onto the head of the cock sticking through the hole and used my hand to rub it around his shaft. Not really knowing how to pleasure a man, and not used to the awkward angle of a dick facing me instead of what I was used to in stroking myself I clumsily started jerking the strange cock using pressure that I enjoy myself. Katy couldn't believe I was actually doing it. She immediately took my dick into her mouth and started humming while watching intently as I stroked the stranger. After just a few moments I felt the stranger stiffen up, I pointed the head of his cock towards Katys face and jerked faster until he shot his load, hitting her face and neck as she sucked me.

I let go of the strange cock as Katy watched it disappear back through the hole and withdrew my own dick from her mouth, handing her a paper towel to clean the cum off of herself and using another to clean my hand. Katy said she thought that was hot and was glad I'd jerked him to completion because now she didn't have to. I told her she wasn't getting off that easy just as we heard the door open to the booth again. I knew that would happen as word travels fast when a woman is playing in a glory hole. I told Katy there would be no shortage of dicks to play with all night long if she wanted to, pointed to the hole and said "your turn".

Not bothering to get off her knees, and now knowing how to fish for dick Katy ran her fingers around the hole for the second time. We immediately heard the unmistakable sound of a zipper followed by the second cock of the night sliding through the hole. It wasn't nearly as long as the first, but was very thick. Katy could barely get her fingers all the way around it. She lubed it up as I had the previous one, held the dick very close to her face and looked me straight in the eyes as she started jacking off the stranger with one hand while scratching his balls with the other. With pure lust in her eyes, Katy gave me a coy smile and asked "is this what you wanted?" I could only nod my approval as I gently pulled on my own member while watching the love of my life jack off the strangers dick.

Katy is obviously much more adept at how to please a man than I and had the stranger ready to cum in no time. Determined to get back at me, she pointed the cock in my direction and asked the man through the wall to cum for her as she jerked him furiously. Her aim was good as the first shot hit me in the thigh as she laughed. Katy finished the stranger off with her hand then crawled over to me to clean his cum off of my leg.

We listened as the stranger zipped up and left. Just as Katy was about to say something, the booth door opened and closed again. After hearing it lock Katy couldn't help but peek through the hole, informing me there were now two men in the booth together. I immediately asked if she wanted to stay and play some more. Katy said she'd try one more and again ringed the hole with her finger. When a diminutive fella dropped his pants and stuck his completely hard three inch dick through the hole, Katy tried to jerk it but just didn't have room to move her hand. Finally giving up she apologized to the guy, gathered up her bag and asked if I was ready to check out that theater.

I didn't have to be asked that question twice as I took Katy by the hand and led her out of the booth toward the theater ticket booth. I purchased our tickets and led her into the straight theater. We stood at the back for a couple of minutes to allow our eyes to adjust to the theater that was pitch black except for the light on the screen. Katy noticed there was a fella on his knees giving alternating blow jobs to a couple of other patrons and asked if we could go sit down. I led her down the isle and choosing a row around the middle of the theater we took seats about mid way down.

Katy's presence didn't go unnoticed for long. Two men moved into the row directly behind us and two others to the row in front of us. As we watched the action on the screen of some sort of Roman orgy, I undid the remaining couple of buttons on Katy's shirt and pulled it wide open for all who cared to view her magnificent tits. I unzipped my own pants and pulled them to my knees. As Katy grabbed a hold of my erection, I gently pushed her knees apart. At first reluctant as she had seen the two men in front were staring at her, she relented saying they could see her tits anyhow, may as well give them the whole show. I again took Katy's new toy from the bag and inserted it while she rubbed her clit with one hand and jerked my cock with the other.

Katy whispered to me that she thought the two guys in front of us were jerking of watching us, to which I chuckled and told here there were to more standing over her shoulders doing the same. Turning to look, Katy almost hit a cock with her cheek the guy was so close. I asked if she was ok with everything and she said yes, she was fine.

One of the guys behind Katy gently touched his cock head to her cheek and started spurting, catching her by surprise. As cum ran down her cheek to her tit the guy on the other side also unloaded, hitting her in the hair and ear which dripped to her shoulder. Watching this and assuming it was ok to cum on Katy, one of the guys in front of her stood and aimed at her as he shot his load over the seat hitting her in the belly. Finally the last guy stood and shot his load on her leg.

With her admirers spent and gone we settled in to watch the flick and continue our own play when an attractive man who appeared to be in his mid forties, wearing a business suit asked Katy if he could sit on the other side of her, promising not to touch her. She said it was up to me so I motioned for the guy to have a seat.

He was very polite while he watched us and told Katy how hot he thought she was. He even asked her permission before pulling out his dick to masturbate. I asked Katy if she wanted to jerk the guy off, she didn't need to be asked twice grabbing hold of his cock and matching the rhythm of strokes she was giving my dick. He asked if he could rub her clit to which she responded "please do". I removed Katy's hand from my cock and moved between her legs and rubbed the head up and down her pussy lips while her new friend worked her clit until Katy had a rather loud shuddering orgasm. I asked if she wanted to suck the stranger as he had been so polite but she declined though agreed he deserved something special.

Getting on her knees Katy had him stand in front of her as she lubed up his cock. Katy then wrapped her tits on either side of his hard on and asked him to fuck her tits, to which he happily obliged. When he got close he asked if he could cum on Katy. She said "why not, everyone else has, where do you want to put it?" He indicated he like to cum on her ass so she turned around and wiggled her ass at him while taking me into her mouth. The man got down on his own knees on the sticky floor of the theater in his suit pants and all and began rubbing his well lubed cock across the crack of Katy's ass. Just as he started covering her ass and lower back with sperm, I pull my own cock from Katy's mouth and shot a load on her forehead that dripped off her nose followed by another on her lips which dripped off her chin.

Katy didn't even bother buttoning her blouse back up as we left the theater. After calling a cab we walked out of the theater, Katy scooped a bit of my cum off of her chin and licked her finger while winking at the clerk on the way out of the bookstore. While waiting outside waiting for the cab I told Katy how sexy she looked covered in cum and resumed rubbing her clit. Once in the cab, she unzipped me and sucked me hard then climbed on to ride me declaring she needed to be fucked now, and told the driver she didn't care where he drove but not to get to the hotel until after she was done.

We finally got back to the hotel where I laid my beauty on the bed and removed what little clothing she had on. I asked her to wait until morning to shower just before eating her to another orgasm. We drifted off to sleep, completely spent with her on my shoulder still covered in strangers cum. On the trip home, all she could talk about was when we were going to make another trip to Boston.