Please note, this is a true story. However, I’ve changed the names, ages, occupations and places to protect the other person’s privacy. I have no shame so enjoy, LOL.

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Pam: The Thrill of Getting Caught 1

Starts slow, ends with a big twist.

Saturday evening, we were headed to a big event. I had just started seeing Pam, a 31 year old admin manager. We met when she attended a conference her company was having in the hotel I just got a job managing at. I had recently moved back to the area for the summer of my 27th year standing. She was 5’6, 32C with long brunette hair and a small yet round rear.

After a few weeks of dating she invited me to a celebratory event. Pam’s aunt and uncle were having their 25 year anniversary. It was being held at a really nice estate in the hills. They had worked for decades at for a large financial institution. As a thank you gesture, one of the execs threw the party for them at their large estate.

The place looked like a mansion you’d in see those dating reality shows are filmed at. Multiple levels, 8+ bedrooms plus several other random rooms and a large yard with a heated pool. It was a catered affair with, wait staff, bartenders, security, valet parking and a door host checking names. The landscaping was obviously well kept. And everyone was dressed to impress.

Pam was wearing a sexy black dress that gave me the right “access”. It had 2 thin straps on the shoulders, with some soft fur that went around the body above the chest. The length was to the middle of her thighs with a small visible slit at her left thigh. She wore a tiny Y shaped thong underwear that barely covered anything. And with the fur covering her top she had no bra on.

I was in a custom made black suit with a royal blue shirt and a striped, grey tie. I was looking good and feeling good. I was feeling even better when I picked up Pam and saw what she was wearing. There was no way I wasn’t going to fuck her wearing this dress and at this event. The question was where, when and how without getting caught. But the risk of getting caught heightened the sexual arousal.

Security cameras were an issue but they were mainly on the exterior. I would have to navigate a few before the evening was over. But inside I didn’t see any obvious ones. Just in case I had to make sure it would be in the darker rooms as at this time period cameras with night vision capabilities were not as commercially available. The last thing I wanted was for Pam to have to face her judgmental firing squad of a family over our escapades. But the risk for both of us was so exciting that the risks outweighed any hesitation.

As we arrived and met many random people. At 7pm, just as the festivities and speeches were to begin. Moving around the huge mansion, I scouted the location as if I was casing the joint. In a way I was but not to rob it. I was going to fuck Pam everywhere I could and as many times as I could this long evening.

After an hour of quick toasts, speeches, meeting people and touring the mansion, I had developed a plan. During that hour we ate, drank, mingled and I scouted the hell out of the place. I walked around making myself look like I was some sort of architectural guy admiring the structure as not to make people suspicious. Several, “wow this is so well made, look at the detail on this trim and man I can’t wait to have a place like this” types of comments throughout the night.

The speeches were too short and Pam would’ve been noticed if she was gone. So after everyone started dispersing around the house it was more riskier that someone catches us. Fortunately, the house size to guest ratio wasn’t too extreme. And there was plenty of places I could do what I wanted. It was just more about the timing.

The first opportunity presented itself when right as the last toast happened, everyone scattered to different parts of the house. So it wouldn’t be too suspicious where we would go. We snuck into one of the 3 garages. This one was the furthest away from the main house. But it wasn’t having Sex in the garage that would be adventurous. It was on what?

There in the corner sat an all-black Honda motorcycle. It looked more like a Harley style then the crotch rocket sport type bikes. It had a small smooth slope upward from the seat to the handles then the big dip in the seat to the front. This was not going to be easy, trying to do what we were going to do. But we were determined to fuck on this bike.

I throw my jacket on a counter and rip off Pam’s thong. I lift her butt onto the leather seat and began eating her out. She was laying facing up with her head toward the front, by the handles. The bike had a longer seat to lay on and eating her out while I was somewhat standing, hunched over and behind the bike. I popped my head up quickly to tell her to pull out her breasts and fondle them.

Seeing her from my angle playing with her breasts and moaning in pleasure was so Hot. My tongue was licking under her hood. Her body was aching for more and my fingers gave that to her. Pam was very wet and I slid in a few fingers. Now I was licking and finger fucking her while she was playing with her breasts. Pam was purring in bliss.

“Do you want me to fuck you?” I asked her.

“Yes, very much so.” She moans out.

“How badly do you want me?” I asked in a more serious tone and increase my fingering pace.

“Very badly, very badly, please don’t tease me. Just take me.” She replies, now frantically wanting to fuck.

The naughtiness of the whole situation then adding in what I was doing to her Pussy had her riled up. Sometimes the where your fucking makes the actual fucking even hotter. And man was her body and desires sizzling right now. I bet she’d even let me fuck her Ass if I wanted. But she wasn’t prepped for that tonight. So my hose would have to put out the fire at a different entrance she has.

I turn her over, face down onto the motorcycle. I move her body further up on the seat. I climb on and put my raging hard cock at her Love tunnel. Her hands are on both handle bars. My cock moves all the way into her. Then I have her fuck me on the bike.

How, well I had Pam slide forward then back her rear up on my cock. A bit difficult at first but once we got a rhythm going, it was on. Slide forward then back, slide forward then back. Then I spanked her Ass for her to speed up. She started pushing back faster and with more force. It felt good but looked even hotter watching this.

I started using both my hands on her rear. Alternating spanking her right cheek with my right hand. And vice versa with the left. Doing this started revving me up and I had to take a more active role in fucking her. I startled her by picking her up and dropping down on my cock on the seat. My face was buried in her chest while she started bouncing and bouncing and bouncing on my cock.

All this was a new adventure and sensation for Pam. She was like a new wild woman riding my cock. Her moans were getting louder but she didn’t care. I pulled out a condom from my shirt pocket and I slipped it over my finger. It was a Durex lubricated condom and right when I knew she would be close to her climax, she’d get another surprise.

My mouth began to sink down hard sucking on her right nipple while my left hand was pinching her left nipple. Pam was ready and telling me, “I’m going to cum, I’m going to cum.” Just as she was about to cum I slipped my condom covered finger into her asshole. Her body was getting so much stimulation from the moment, my cock, my mouth, my hand and now a finger.

“Holy fuck!” She screamed out loud as her climax hit. But I didn’t stop my onslaught on her senses. She stopped riding me and just sat there for a bit. My finger didn’t let up and neither did my mouth. But then we hear someone say, “Check over there.” We get off the motorcycle and climb into a H2 Hummer.

There we were hiding on the floor of the back seat of this gigantic car. A person with a flashlight walks in and starts to scan the garage. Pam is holding my hands and were both smiling at each other. After a few minutes, the person with the flashlight leaves. I guess Pam was so loud security from the main house came over. She jokingly tried to say it was my fault but my response…..”It wasn’t my voice; my mouth was busy sucking on your breast.

After we came back into the main area, we got separated a bit as some of her family grabbed her for some photos. I moved back to the kitchen to grab some water and hydrate some. I didn’t want to go to the bartender outside as I wanted to stay as low key as possible. The kitchen had a sectional island with a few people small talking. I walked around them to the counter and grabbed a water bottle. An older women approached me and asked me to show her where the bathroom was. When I looked over to answer her, it was Janet!

She was a cougar who literally taught me about exhibitionism and the techniques on how to fuck outside. I was 20 and she was 41 when we met. We had a brief but memorable time together. Now Janet was 48. I remember her juicy 36DD rack was just as desirous to me as it was back then. She was still attractive and I would fuck her if I had the chance.

Janet was wearing a chef’s jacket. I found out she was helping the person who catered the event. So she knew damn well where the bathroom was. In fact she led me to a different bathroom I didn’t even know was there. It was in a fitness room, separate from the main house they set up their supplies in. She was on my arm as we walked there, talking and laughing. Both knowing what she wanted. And heck I’ll admit I wanted to fuck her also.

What the hell was I doing? I was here with one date and now about to fuck another. Granted we haven’t talked about being exclusive. But I was at her uncle and aunt’s 25th anniversary. I generally don’t have regrets but I’m definitely on thin ice on this one. In the moment I confess I didn’t care if we got caught and Pam found out. Janet had me wrapped around her finger like I was under a spell for years. I had to have her right here, right now!

When we got inside the bathroom our mouths moved from talking to pleasing each other. I open up her white chef’s button up coat with and her juicy melons come into view. Now there wasn’t a hallelujah and bright lights that appeared in reality but in mind I swear it did. I’m sure her boobs got bigger, I bet she had them done again. I am not ashamed that I went to town on her breasts and tried to suck them dry. I seriously spent way too much time liking, sucking and squeezing them; she had to stop me as she wanted to fuck before people came looking for her.

My pants drop and I lift up her black professional knee length skirt. Wait, she’s not wearing any underwear herself. I wanted to go down on her but she stopped me. I spent way too much time on her breasts already, we skipped anymore foreplay. She wanted me to hammer her, now!

Janet learns over the bathroom sink and says, “Fuck me hard, you know how I like it.” I quickly enter her and notice she’s considerably wet. She stills feel so good down there. As I start hammering her wet Pussy, I realize there is a sense of recognition that hits me. I remember that feeling, that extra wetness. I’ve fucked her enough times to know. It was someone else’s cum inside there.

This means I wasn’t the first inside her tonight. Which didn’t surprise me, when we messed around before she had 3 or 4 boy toys at once. There were several days we hooked up I was either the 2nd or 3rd guy that day and she had their cum inside of her from the others. I can only imagine what it felt like for the last guy that night. Janet was an insatiable cougar, who constantly preyed on younger men for their energy.

While pounding her hard I ask, “So I take it I’m not the first to cum inside you this evening.”

“Your definitely not the first probably the 3rd and I’ll have a few more before the night was over. But you are the oldest.” She replies.

“Your such a fucking wild one and I luv it.” I tell her in an supportive of her getting as much Ass as she wanted and non-judging way.

“Wish you didn’t get yourself a mixed up in a relationship back then, I went through quite a few guys to replace you in filling my noon Sex needs.” She commented.

Most of the guys working as catering staff were 20-24 and colleges kids. That was her usually age range as she loved their youth and energy. Working on a college campus with a grad program she access to guys left and right. One of the guys she used to fuck even ended up marrying her daughter. I wonder if she still fucked him while he was with her daughter.

The thought of that got me even more turned on. I don’t know if I could’ve resisted Janet if I was in that guy’s shoes. There was something about her, some power she wielded over us men. Now I’m fucking her again years later, with her bent over the sink sparking many good memories in my mind. But my body was focused on making a new memory now.

“Do you like my new boobs? I went to 36EE.” She asks.

“Hell yeah!” Was the only response I had.

“Do you still wish you were my noon Sex toy? Do you miss me taking you around campus and the medical offices to fuck me in random places?” She asks.

“Yes, hell yes I miss fucking you daily at 12pm in random places. I miss all the wild times we had.” I confessed to her.

“I know you want to cum on my new boobs but I need you to cum inside me. You know the drill.” She devilishly says.

The drill she was referring to was, whoever was last to fuck her had to eat her out. Janet didn’t even to Orgasm until the last guy of the night. She wanted to have the euphoric feeling/edging all day until she had the massive Orgasm to close out the night. Plus the thrill of some young stud eating her after whoever had filled her up that day was extremely gratifying for her. For Janet that thrill was so electrifying. It was her special kink and nothing else got here off the same way.

As I was pounding her with fury, she told me she didn’t approve of the woman I was with. Her intuition told her Pam was too uptight for me. She literally told me to get my rocks off quickly then move on. In her words there were too many single women for me to waste my time on uptight. Although she was kind of right about Pam, as she was a little uptight. What she didn’t know was I had already been “loosening” her up.

Janet loved the power I had in my hips and my ability to control my movements. She kept pushing me with her words, “Harder, Harder, yes, just the way I like it, harder, fuck me.” The more she said the harder I kept trying to punish her hole with each thrust. It wasn’t long before I grunted out in ecstasy and emptied my load. Adding to her cum filled Pussy. I found out later that she also fucked one of Pam’s nephews that day, which would haunt me at a later time.

We got dressed and kissed some more. Janet had these big full lips that were so fun to make out with. She would suck on your tongue and melt you into her Venus fly trap with those lips. And I was one of those that got stuck in that trap. We went back to the party in separate directions. I walked all the way around from the back side of the garages to the pool area, then smack bad in the middle of the festivities.

Once I came back to the main area, I found Pam talking with a few of her cousins. I wave her over and we went outside toward one of the courtyards. There was a small structure, it was the fitness room I just fucked Janet in. Walking along a side wall, I stopped her and physically manhandled her up against it. The lighting was nonexistent as the wall shielded us from the courtyard lights that were fully lit. It was very dark and a cool breeze was hitting us.

I held my left hand over Pam’s mouth, kicked her legs open and her thong was in her purse. Fingers from my right hand roughly entered her. Pam was still very wet with my cum still mixed in there. This was not a Sex scene for the timid. There was no gentle teasing on foreplay. It was pure lust.

From afar it looked like I was assaulting her. And in a sense I was. I had been aggressively finger fucking her very wet and warm Pussy. Her screams were going into my hand. Hiding the sounds from the world. I could feel the muffled vibrations against my palm.

As I look into Pam’s eyes, the look of intensity she’s giving me is egging me on for more. And so I began to spank her Pussy firmly. Shivers went through Pam’s body as the first strike stung not only her body but also her senses. Her body is on overload from my assault on her Pussy. The climax I was demanding with my actions was about to arrive. But then……….

We hear some ruffling from the bushes. There was someone watching us from the parking lot. It was a person in a noticeable white jacket. I’m guessing it was one of the parking valets. I couldn’t make out at this distance if they were touching themselves or not. But this gave me an idea.

Pam started to tense up. However, I was unrelenting in the assault of her smooth freshly shaved Pussy. I was determined to give her another strong yet unique Orgasm. Another one that she’d remember forever. I said a strong tone, “Let him watch. Let him see you in pleasure. Let him see how Hot you look when you climax. Because I am not stopping until you do.”

With those last words from me, Pam fell back into the moment and let it all just happen. Her body was trembling. I was rotating from finger fucking her and spanking her Pussy. The climax we both wanted to happen was building up again. “Look down at him.” I said while continuing my onslaught.

Her eyes moved back into his direction. I whisper in her ear, “You know, he’s got his cock out and jerking it. Watching you getting finger fucked like a slut in heat. This must be making him crave to fuck you himself. What if I removed my hand from your mouth and let him hear your scream out in ecstasy? He’s probably been watching us the whole time and is now ready to explode.” Now at this point I didn’t know if he was touching himself or not.

Simultaneously, when those words came wickedly pouring out of out of my mouth, Pam climaxed all over my hand. We’d only been fucking for a few weeks but this was the most juices I’ve seen come out of her. Pam fell onto my shoulder. I held her there in my arms. Then we both her a distant groan. So he was touching himself watching us. A big proud smile came across my face. Technically I was now responsible for 2 peoples orgasms with only one hand.

As we gather ourselves and head back to the house. I notice the were gathering most of the people by the pool area. A few of the caterers brought out a large anniversary cake. There was still some stragglers that stayed inside. Some of the men were shooting pool in the billiard room and some randoms throughout the house.

We walked inside like we were looking for the bathroom. I tried to be a discreet throughout the evening as possible so no one would notice us. So if we had gone missing it wouldn’t be as obvious. We headed quickly up the stairs to the using the back stair case and arriving at the top level. Moving down the hall without anyone seeing us and into a large dark room.

While inside I was already very hard from what just occurred. Not to mention I was pretty amped all night already to fuck. I pushed Pam onto her knees, dropped my pants and my shaft started disappearing between her lips. She didn’t notice as I took off my suit jacket but put something in my shirt pocket. In and out of her small yet skilled mouth. Standing above this sexy woman with my very hard shaft being swallowed was such an erotic sight.

I could’ve let her suck me for hours but I was targeting my cum for another entrance of hers that I already left some in earlier. I lifted her back up and moved her close to the window looking down on the pool and other guests. I put her hands and forearms against the wall that was adjacent to the window. We could see down and through the way the windows were tinted. It would be tough to fully see inside without the lights on.