Cassies First Glory Hole

This is my first attempt at a story. I hope you enjoy!

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Cassie and I have been together for about 5 years. We are a very happy couple and have a good sex life. We have experimented sexually with most of the things a couple can do together; toys, anal, Kama Sutra, sex in public, sex in the car, roll play, light bdsm etc. She has always been more willing than me to try new things which helps bring me out of my sexual comfort zone.

She loves being dominated, spanked, choked and fucked hard when we have sex. I always worry about getting too rough or taking things too far, but she has never complained and usually gets more excited when I am assertive in bed.

We have hinted about bringing a third party into the bedroom, well mainly me because of every guy's fantasy of having two girls at once, but since she is a little bi-curious she has never scoffed at the idea. In the discussions she has always said that she isn't one for sharing, so mainly I would get to be a spectator for the two girls, which isn't as appealing for me, but I wouldn't turn down the opportunity either.

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Last week, Cassie had received a call from her parents asking her to come and help out with painting and re-organizing a couple of their rooms. She has a keen eye for design, so she is routinely asked by others for her opinion on decorating ideas. Since I already had plans to clean up my garage during the coming weekend, she figured that would be a good time for her to visit them for a few days.

After work on Friday, I helped her pack her bags into the car, we kissed each other goodbye and she set out on the 3 hour drive to her parent's house in the mountains.

I headed back into the house to start on the daunting tasks of cleaning out the years of clutter that has kept us from using the garage for the purpose it was designed. I grabbed a couple beers from the fridge, turned on the stereo to a popular rock station and got to work. I made pretty good progress in the first couple hours, and had about 3 boxes of stuff that could be thrown out and a couple boxes of items that we no longer needed which could be sold off in our next yard sale. I had also devised a pretty good plan of how to organize the room which would allow us to get one car comfortably into the garage.

Pleased with my progress and sweaty from the effort, I headed into the house to cool off and grab something for dinner. I showered, heated up some left over's from earlier in the week, grabbed a tall Jim Beam with Coke and sat down in front of the computer to explore the world wide web.

As the liquor did its job relaxing me, my internet surfing starting pulling up more and more adult content. At first it was standard couples engaged in the usual positions, but every once in a while I would run across images of a lucky guy in a chance encounter with two girls at the same time. This naturally got things stirring in my pants and I started imagining Cassie and one of her hot friends in all sorts of flexible positions.

My mind was really getting kinky with the imagery when I was jolted out of the day dream by the sharp ring of the cell phone next to me. I looked at the caller ID and saw that it was Cassie that was calling. She let me know that she had arrived safely and was in the process of finishing up dinner with her parents. I told her to have fun, I loved her and that I would text her later when I was headed to bed.

The interruption that brought me back to reality also gave me a chance to get a refill of my drink. I took the refreshed drink to bed and decided to continue my porn surfing in there with my phone since I would surely pass out after I finished that glass.

I flipped through a bunch of pictures of MFF threesomes and found a really hot one that I liked of two young petite blondes. One girl was on her back getting plowed by the guy and the other was straddling that girl's face. I decided to text the picture to Cassie to toy with her a bit. Since she was with her parents, I expected her to respond by telling me that I was a horn dog and to stop messing with her.

After a couple minutes my phone beeped and I was surprised when she responded, "Mmmmm...looks yummy!" with an emoji sticking its tongue out. I guess she was just as horny as I was, so I found another image and sent it to her, which got a similarly naughty response. This went on for about 10 minutes, before I started struggling to find good quality pictures that I liked. In the lull, she texted me, "I want some more!!"

I continued to flip through the pictures to find more good ones, and as I did I took another drink because I was getting parched from the excitement. During my sip, the phone surprised me with another beep which made me lose a grip on my drink. I managed to keep from dropping the glass, but during the process I had fumbled the phone and it bounced off the bed and onto the floor.

I put the drink down and quickly picked the phone back up. It was unharmed but I noticed that during the fumble I had inadvertently closed the page where I was viewing pictures. I saw the preview of the text Cassie had sent which stated, "Give me more, sexy!!"

I went and grabbed a towel to wipe up the few drops of my drink that had escaped when I almost dropped the glass. When I returned I heard the phone beep again. As I blotted up the moisture from the comforter, I looked at the preview of her message on the phone which read, "Now that is HOT!" I was a little confused at her response, since I hadn't found any new pictures to send her recently.

I picked up the phone, and opened the texting application to ask her what was so hot. On our conversation screen I saw a picture of a guy doing a girl doggy style while she was blowing another guy. I thought to myself, "Where did that come from??" I realized that I must have accidentally pressed some buttons and sent that picture when I dropped the phone earlier. I wonder if that is what she was saying was Hot?

We had always talked about bringing another girl into bed with us, but I had never really thought of another guy since I am not bi-sexual. I'm not sure I could remain aroused seeing another guy naked in the same room with me. In my inebriated state, the thought of Cassie sucking another guys cock while I fucked her or vice versa was actually making me mighty hard.

I decided to test out my theory. I found a steamy video of a pretty girl getting banged by two well endowed guys in multiple positions and then I sent her the link. About 10 minutes passed and I started to wonder if I had made a mistake. I figured I misunderstood her earlier text and now she was upset and giving me the silent treatment.

Just when I was about to send a text apologizing, my phone beeped with a new text message. Her response was, "Just say when!" with a devilish emoji. My mind went crazy with the thought that she wanted to have sex with another guy, but it also turned me on to no end! All the new images that flooded in my head got me so excited that I had to go relieve myself multiple times to get me to the point where I could actually sleep that night.

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In the morning, I woke up in a haze. I tossed and turned most of the night which didn't make for the best sleep. I wondered if I had just dreamed the texting exchange from the previous night. A quick check of my phone proved that it had really happened. I made a cup of coffee and tried to put the encounter out of my head so I could focus on the garage cleanup.

By late afternoon I was able to get shelving built to better stack the boxes of stuff that we needed to keep. I had gone through most of the boxes and got them organized on the shelves. All that remained was arranging my tools and my work bench which shouldn't take more than an hour to finish up. I decided to move on to some yard work and save the last bit of the garage for tomorrow since I needed some of the tools for tuning up the yard equipment.

That evening I met up with the guys at the sports bar for some wings, beer and football. On the way home, I heard my phone beep announcing a new message. I figured one of the guys was giving me shit about my team getting slaughter that night.

At the stop light I glanced at the message and saw it was from Cassie and it contained a picture of her lying on her back naked on her parent's spare bed. She had a red dildo in one hand being buried in her pussy and a blue one in the other dangling over her face as she licked the tip. I was shocked since I she only owned one dildo and I know she didn't take it with her.

The car behind me honked to bring my attention back to the road and I continued driving onto the next red light. As soon as I stopped, I grabbed the phone and texted her, "Where did you get the studs?"

She responded, "I stopped by an Adult video store while I was out today, so I could try out your idea!"

The bulge in my pants started growing again and I raced the rest of the way home. When I got there I got ready for bed and checked the phone. She had sent me a text saying, "I got my hands full, Send me more naughty pictures!".

I scrolled through more pictures and sent her another one of two guys having their way with a girl. She responded, "Oh yeah!". I looked around some more and found a pretty good gangbang site. From it I sent her a picture of 3 guys filling up all of a girl's holes.

She responded, "YES, fill me up!".

I sent her a couple more with 3 and sometimes more guys and she replied, "I'm getting close, take me over the edge dirty boy!"

For the grand finale, I sent her a video of about 8 guys taking turns getting blow jobs from a girl and dousing her with cum while she was on her knees begging for more. It took Cassie a couple minutes to respond, but when she did she said, "Oh, God...Mmmmm...I want you to cover me with your cum like that!!".

Her final text was, "Thank you, you wore me out! Sweet dreams and I will see you tomorrow evening for the real thing!"

I started getting a sly idea from our exchange tonight. I ran to the computer and started hatching a plan for her return tomorrow evening.

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I searched for the adult video stores in our area, and found three of them that were nearby. I noticed the one that we got her current dildo from was on the list, but I knew they didn't have what I was wanted. I checked the other two and found that the one on Wilshire Drive had back rooms with video booths. Perfect!

I read up on some of the reviews of the place which gave it decent reviews for cleanliness and movie selection. I saw that there was also a forum for the video store and I posted a question asking, "When is the best time to visit the booths?" Within minutes I received a bunch of responses. Most of them said that around 9pm was the best because it was before the crowds of guys came in.

One of the forum members private messaged me and we got to chatting about the facility. He was a wealth of knowledge, telling me the cost, which booths were the biggest and which ones had glory holes in them. I told him my plan and he said that he might have to stop out there for the event and bring some of his buddies.

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The next day I rushed to finish up the garage and made sure the house was clean. Then I spent time gathering the items for the evening's activities. I laid out a tight black spaghetti strap dress for her to wear that would barely covered her ass and her best stripper heels. I also put a couple of towels and a blindfold in a duffel bag and placed it in the trunk of my car.

Cassie texted me around 5pm and let me know she was about an hour away, so I went and showered and got myself ready for the evening.

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She arrived home around 6pm and I helped her unload the car. She raved about what a great trip it was and insisted that I go with her next time. I said, "I would" and gave her a nice long kiss. I could tell she was horny because she didn't want to break the kiss and she started groping my ass and trying to reach for my zipper. I pulled away and said that she had to wait for later. She pouted a little, but she knew I wouldn't make her wait for long.

I sent her to the shower to get cleaned up so we could go out to her favorite restaurant. When she got out, she saw the outfit that I picked for her and she gave me a sly little grin. She went to the dresser to get panties and a bra, but I told her that she wouldn't need them tonight. Her sly grin went from ear to ear this time.

When she finally emerged from the bedroom, my mouth dropped. She was stunning, and I could see every inch of the curves on her luscious petite body. Her long red hair was shimmering and the low cut of the dress barely covered half of her firm B cup breasts. I could even see a hint of her nipples and knew that they would definitely be visible when she got excited!

At dinner we sat next to each other in our normal booth in the corner and she told me about the decorating she did at her parents and how much they loved the paint colors she had chosen. She told me all about her father's new business venture and how well he was doing with it and then about her mom's new car that she had just gotten. I kept feeding her wine as she talked and I could tell that she was getting tipsy because she was more giggly than usual.

When the conversation slowed, I reached my hand over and put it on her knee and reminded her how beautiful she looked tonight. She blushed and turned away a little. I slowly started walking my fingers up her inner thigh and I could see her eyes shoot back at me and widened.

I leaned towards and and I asked, "Did you bring your new toys back with you?"

"Of course I did, do you want to watch again?" She said as she licked her lips

I said slyly, "No, I have my own plans for you tonight."

As my hand started under the hem of her skirt she parted her legs to allow me access and I could feel the moisture between her legs. I could also see her nipples tighten under the dress and start to show.

She leaned over to my ear and gave a slight moan and said, "Well let's get to it handsome, I'm ready."

I paid the check and we headed out the door. In the parking lot I took every opportunity to rub her firm ass as I walked behind her. She playfully picked up the pace, but I caught up to her at the car and we embraced in a long kiss as our hands explored each other's body. We only stopped when we could hear distant voices from other patrons leaving the restaurant.

I helped her into the car and walked around the back and popped the trunk. I took out the blind fold and closed the trunk back. I got into the driver's seat and her hands were all over my crotch and kissing my neck while I struggled to latch my seat belt. It felt so good, but I had to ease her away. I could tell she was disappointed, but then I rose up my hand and displayed the blindfold and told her to put it on. She gave me a puzzled look, but took it and put it on over her eyes. I made sure she couldn't see and then I put the car into drive and headed out of the parking lot.

During the drive, she repeatedly asking where we were going. I refused to tell her, but I said that she would like it. I could see she was excited and I reached over and rubbed on her supple breasts, lightly pinching her nipples and making her squirm in the seat. I continued to explore her body to keep her mind off of the surprise. I looked at the clock and it was 8:55pm when we pulled into the parking lot of the video store. There were only 5 cars in the parking lot so I knew the information my forum buddies had provided was accurate.

I eased the blindfold from her eyes and she blinked to regain her focus to read the bright neon sign. She looked over at me and said, "Why are we here, I just bought new toys?"

I told her, "We aren't here for toys."

We got out of the car and took the duffel bag from the trunk. She stared at me with the same puzzled look she gave me in the car. I held her hand and followed me into the store. I could see the male patrons instantly turn their attention to Cassie in her tight fitting outfit, and I'm sure they noticed her erect nipples peaking through the thin material. We headed straight to the counter and I asked for a booth. I handing the attendant the required $10 fee and he directed us to the curtain behind him. I knew he was staring at Cassie's ass as she passed, but I think she was enjoying the attention.

When we went through the curtain she pulled close to me and asked where we were going. I comforted her and told her to wait and see.

We walked down the dimly lit hallway and I could hear moaning from multiple booths that had movies playing. As we passed by the first couple booths we could see guys in there stroking themselves to the sex acts playing on the screens. They didn't pay any attention to us and we continued on...3...4...5. My buddies on the forum said room 5 was the cleanest and was a little bigger and had two chairs. The room was unoccupied so we went in and shut the door.

Cassie seemed a little scared, so I put my arm around her and gave her a nice soft kiss which relaxed her. I pulled out a towel and laid it across our two chairs and sat her down on the left one. I grabbed the remote near the screen and sat down next to her. I slowly flipped through the channels of couples having sex, lesbian sex, interracial sex...all of which looked good, but I was looking for something specific.

After a few more channels I finally hit the channel I was looking for. On the screen was an early 20's petite Asian girl sitting on a couch with a group of 4 guys. They descended on the lone girl and were groping ever inch of her as they undressed her and she took a cock in each hand. Cassie's eyes widened and became fixated on the screen. Her hands instinctively started rubbing on her breasts and I could see her shift in the chair. I put my hand on her thigh and pushed her skirt up and started rubbing on her freshly shaven mound. She spread her legs and gave me access to insert my finger and slide it in and out of her.

She slid the two spaghetti straps from her shoulders and released her tits so she could massage them as she continued to stare at the screen in amazement. Cassie watched intently as the guys took turns filling the girl's mouth and pussy with their members. I leaned over and kissed on her neck as I navigated another finger into her soaking wet pussy. She took a deep breath grabbed my face and kissed me wildly as I worked my fingers in and out of her pussy. Her breathing got very heavy and she grabbed my hand between her legs and held it tight in its current position as she experienced her first orgasm. She shook heavily and almost fell out of the chair, but I was luckily able to keep her seated.

As her orgasm subsided, I pulled out my fingers and she nibbled on my ear moaning, "I want your big cock in my mouth, NOW!". I stood up to drop my pants and give her what she wanted, when I looked over behind her and saw a 6 inch semi-hard cock protruding through the wall. I leaned over and whispered into her ear, "I think someone else is ready for you first". I turned her around and pointed to the hole in the wall. She peered closely at what I was pointing at and then jumped back a little when she realized what it was.

She turned back to me and asked, "Really?".

"That's what we are here for." I said

I stood her up, moved the chairs out of the way and laid the towel from the bag down on the floor under the glory hole. I slid the remainder of her dress down and over her hips and let it fall to the floor leaving her completely naked, with the exception of her heels. I gave her another deep kiss, cupped her breasts and told her that we were not leaving here until these were completely covered with cum. She gave me a coy look and said, "Challenge Accepted!"