I decided to read my older stories and realized how poorly they were written. So, I rewrote this one to improve the detail and correct some inaccuracies. If you've read this story back in 2012, it is much better now! At least, I hope it is. lol

It’s been a few months since my girlfriend Sara’s awakening trip to Vegas (See Previous Story), and life has been great! She loves that I’m okay with her satisfying her lust for other men, especially if they have large cocks, telling me how much she loved me for making her feel comfortable enough to express her innermost sexual desires without judgment. Another thing we both learned about ourselves after her Vegas trip was that we both got exceptionally turned on by her sending me the teasing photos and videos while I was experiencing it remotely.

Life was returning to the normal swing when I had to travel to Dubai for business. Before I left, my girlfriend kept hinting that she wanted to try something new in the bedroom. During the weeks leading up to my trip, she started testing out a new fantasy with me during sex about her fucking a much older guy and also “giving a treat,” as she called it, to a much younger stud. When we roleplayed the idea while searching porn in the genre, we discovered we both loved the fantasy, so I encouraged her to find the right guys. 

I then reiterated how much I’d love for her to satisfy all of her fantasies or at least try them once. She loved how I reacted to her new fantasy. Before I left for the airport, my girlfriend wanted to have sex one more time, and to warm up had me watch a video of a young Russian girl giving an older man a blowjob. Then we had sex for the last time. I wouldn’t fuck her again for at least a week. I have to admit the video was very hot to watch, and I felt like it would be a great fantasy to explore when I got back home.

After hours and hours of travel from LAX > NYC > Dubai, I finally landed. The flight was enjoyable with Etihad Airlines, and what added to the enjoyment was sitting next to a beautiful 18-year-old brunette girl who reminded me a lot of a younger version of Sara. She was extremely friendly, and we spoke throughout the flight to pass the time. As we shared stories about our lives, my mind would often drift to our age difference and the video Sara had me watch before leaving the house. 

I was twenty-nine years old at the time of this story, so not twice to three times the girl’s age like in the video, but I thought about all the dirty things I’d do to her if I were single. Also, the fact we were staying at the same hotel replayed what might have been in my mind. To be clear, I’d never cheat on my girlfriend. I’m not that type of guy, but if most guys are being honest, they secretly think of sex when an attractive girl is nearby. Once we deplaned and I turned off airplane mode, I received a text with a picture of Sara posing on our bed in her sexy lacy lingerie and garter belt. I knew she was up to something naughty again, so I quickly replied:

Jack > “I hope you’re having fun with Ty.”

(For those who haven’t read the previous story, Ty is the name of her 10-inch Black Marcus Suction Cup Dildo she bought to cover up her fucking Ryan).

Sara > “I have him inside me right now, and I love how he stretches my pussy out, honey! I’m so full!”

Jack > “I wish I were home to see it, babe! :O Can’t wait to get back to you!”

After exiting the airport, I immediately went to work, connecting with my colleague and good friend Amir, who worked with me on several projects over the years. After an hour of early morning meetings, I was dying to connect with Sara again as we arrived at my hotel to check in. I knew she was up to something, and I couldn’t wait to get to my room since my meetings had finished for the day. When I was able to check my messages, I opened the app to find a photo of my girlfriend completely nude, holding her camera from below. Her dildo, at this point, was suctioned to the wall of our bathroom shower as she backed herself onto the large black rod.

There is a 12-hour time difference between the UAE and the west coast of the US, so I knew that around noon, I’d receive additional photos of that night’s activities. Unfortunately, I had to meet back up with Amir instead of spending time flirting with my beautiful sexual girlfriend because of a last-minute meeting. As I left the hotel, I greeted him again when he asked, “How’s Sara doing? Are you guys still together?”

He met her at a business dinner before we started dating. Initially, he was the guy hitting on her, trying to get her to sleep with him. So I gave the guy a thrill and showed him the last photo she sent me, saying, “She’s doing great! Still teasing me while we travel like usual!”

Amir immediately grabbed my phone when his jaw hit the floorboards of the rental car in amazement. I knew he was adulterous and crude toward other women, often paying for companionship when we traveled. His eyes snapped to mine, and he said in broken English, “When I visit you in California. I want a piece of that! Damn Man! Fuck! And to think I could have been in your shoes!”

I laughed and replied, “Well, I owe you for being my wingman with Sara!” I paused, thinking of another situation from our past, and continued, “And I guess I owe you for that girl in New York also!”

In NYC, before I met Sara, Amir and I shared this young, petite, model-looking blond girl after a night of “models and bottles,” as he called it, at Marquee Nightclub. I was already in bed asleep when they showed up at our apartment drunk. He didn’t have to involve me but decided to wake me up and coax me from my bedroom to introduce me to her. 

Long story short, the girl was extraordinarily horny, and I was able to experience her talented oral skills. I sat on the far left side of a long white leather couch with the Empire State Building lit up behind me while Amir fucked her doggie style, kneeling on the floor behind her while she was on her hands and knees with her head bobbing up and down in my lap.

We laughed at the memory and crazy night and proceeded to our meetings. After our meetings, Amir couldn’t get the image of my girlfriend nude with her dildo out of his mind, so he mentioned wanting to see more of Sara’s photos. I showed him a few more pictures from the series of her flashing me in the shower before we parted ways. I rushed back to my hotel to Skype with Sara and hopefully get more photos. When she answered the video call, I noticed she was wearing a skin-tight black cocktail dress with her fantastic D-cup breasts pouring out of it. She greeted me with her gorgeous smile and an air kiss before saying, “Hi honey, I had such a great night!” She seemed a bit tipsy, and I wondered how much she had to drink.

I asked, “Tell me about it! I’m sorry I got tied up. What did I miss?”

She replied, “Well, since you left me feeling horny and alone, I hope you don’t mind, but I decided to meet up with Richard.” She continued before I could say anything, “He messaged me when you ignored me, and he invited me out for a night on his yacht.”

We would often fantasize about her servicing her clients in more ways than just meetings and paperwork, and he was one of those older guys we’d roleplay about during sex before my trip. The best way to describe him is a wealthy investor, playboy type guy, who drove a white Ferrari F458 Italia and was rumored, according to Sara, of having a very nice fat cock by her friends. 

Hearing she met Richard on his yacht alone made my cock stir, and chest tighten with excitement. To describe him further, he is 58 years old and a handsome guy for his age. You could tell the guy worked out daily; very muscular, tall, and well-known around town. The last time I met him was at a charity harbor cruise, where she introduced him to me officially. Thinking of my younger thirty-two-year-old girlfriend going on the yacht with this older guy got my pulse to quicken.

She said they had a great time and took the boat around the harbor several times while they ate dinner. During dinner, he kept complimenting her on her figure, and she told me she knew he wanted her. So she decided to make the first move, asking him point blank with a naughty smile on her face, “What are you looking at?” She paused as he tried to explain, sneaking a peek at the top of her exposed breasts as she continued playfully, “You want to fuck me, don’t you?”

Initially stunned by her forward question, Richard said, “Of course I do; what guy wouldn’t?”

Sara knew from her hot co-worker girlfriends that he also threw crazy sex parties on his yacht during the summer, so she knew he wasn’t shy in that department. Amused by his answer and seated right next to him, she reached her hand over under the table, finding his hardening crotch as she started rubbing his cock through his slacks. She then said, “Mmmm, Jamie mentioned you had an amazing cock. I want to see it!”

Richard said, wrapping his hand around my girlfriend’s waist, “Oh, she did, huh? Don’t you have a boyfriend, little girl?”

Sara recounted their conversation later to help me write this. She said she found it funny that he called her a little girl when she was thirty-two.

When she told me this story, my heart was racing, and I couldn’t help but imagine the scene and wonder who was driving the boat! She laughed, finding it amusing that I’d ask that, then said playfully, “So the idea of me pulling his zipper down and fishing out his older big cock to stroke doesn’t interest you, huh?” We laughed when she continued, “The boat captain, of course!”

The Captain was a good friend of Richard’s, and at the time of her caressing his cock, he was one floor above them driving the yacht. She then described the Captain as handsome in his late 50s. After explaining the Captain, Sara shifted her focus back to describing the flirting between Richard and her. She told me that when she first grabbed his cock she knew she’d love his size inside her. He wasn’t as long as the black men my girlfriend fucked in Vegas, however, he had an attractive-looking, very thick 8-inch cock. She said that the excitement of having a much older man fondle her younger body and her stroking his cock under the table made her heart race! 

She stopped him from touching her and got up, pulling him inside the lounge to dance for him as he sat on the couch. My girlfriend was acting like a high-priced stripper but free of charge. At this point, she loved being a slut for me and especially loved the guys she was with to photograph her, so she offered him her iPhone and told him to take photos for me.

Richard was amused and confused when he responded, “For your boyfriend? Damn, I didn’t know you guys were like that! Love that!”

Richard was in shock, initially thinking she was a good conservative girl that he’d have to corrupt to sleep with, but loved that she was secretly a nympho and that I was secretly a cuck who enjoyed seeing the photographic evidence of my girlfriend with other men. After taking a few photos, Sara took her phone from Richard and sent them to me. 

My phone vibrated with another text message. It was a picture of Sara in a black cocktail dress, straps off the shoulders and almost fully exposing her breasts to him. The image’s background showed the harbor’s shoreline through an open sliding door to the lounge, and I could tell she wasn’t wearing a bra. After seeing the first photo, I had already shed my clothes and was stroking my rock-hard cock at full rate, imagining what pictures she might send next!

The following image was my girlfriend topless, bending over and giving him an air kiss. Then the next was of her backside facing the camera, bending over at the waist, lowering her dress past her knees, and showing off her tiny black panties, which barely covered her pussy. She stopped telling me the story abruptly and said, “Honey, that’s all for tonight. When you get back, I’ll tell you the rest.” 

At first, I thought she was joking, but then she said she had to go to bed since she had work early the next day. I was very disappointed. However, my imagination kept running wild with what she might have done to him that I came so hard it flew nearly to the other side of my hotel room. Just the idea of her letting Richard fuck her drove me crazy!

Story Update: December 2024

I later learned that the Captain eventually docked the boat and caught Sara and Richard having sex on his lounge couch. According to Sara, she especially loved it when the guy walked in on them fucking, and admitted she didn’t stop riding Richard’s fat older cock as she looked over her right shoulder, making direct eye contact with the Captain. Initially, she thought the guy would leave the boat, assuming Richard wanted her to himself, but she was surprised when, without asking her permission, Richard offered to share my girlfriend with this stranger. According to her, she spent most of the remainder of that evening fucking the Captain, not Richard, since he came quickly. I had to ask where, and she told me they both fucked her raw and came deep inside her pussy.

Back to the original story:

The next day, I woke up to her texting me that she wanted to share her experience with me tonight and to be available around 10 pm, which would be 10 am my time. Luckily, I didn’t have any meetings today to ruin it, so I quickly jumped on Skype when the time came. She answered in a dark luxury-style bedroom of a beautiful house and wore a sexy skin-tight dress like she wore to the local nightclubs on her girl nights out. It’s a beach town, so I figured there were a handful of clubs they went to, which was upscale enough to explain her attire. After taking in my girlfriend’s beautiful smile, she said, “Hey, honey, are you ready for another surprise?”

At that moment, from the right side of the laptop camera view, a very attractive “pornstar-like,” as Sara put it, cock of about 9-10 inches long and thick came into view next to her face. The image that struck me was how massive the guy looked so close to the camera. His cock was so heavy it curved his massive erect shaft downward toward the floor while his tip had a thin line of pre-cum already drooling from it. My girlfriend smiled at me in amusement and asked if it was okay for her to suck this cock.

I asked her whose cock it was, and she refused to answer and instead wanted me to guess. I said, “Well, it can’t be Richard since his cock is supposedly eight inches long, and this cock seems to be much bigger and darker in color.”

She reached up, encircling the root of the strange guy’s cock before lifting his heavy shaft upward, pointing him toward her parted lips as she started slowly stroking the mystery man’s entire length. She said, “It’s not Richard’s, Ryan’s, or the captain’s, guess again.”

Amused by her playfulness in mentioning the Captain, I responded, “Okay, is it someone I know? Or met?”

Sara moaned, smiling, locking her eyes on the tip of this guy’s cock as she played with the pre-cum at his tip. She then licked her lips before confirming that it was someone that I knew. My mind was racing, trying to figure out whose Latin, Arabic, or Indian cock this could be, and she asked again, “Babe, can I please suck this huge, amazing cock for you? I want it!”

I took the opportunity to instruct her and told her that she could lick the tip only until she told me whose cock it was. She then said, “It’s someone you’d never expect. And this isn’t the first time I’ve sucked his cock.”

I remember her mentioning being with a large guy in the past when she was younger, and my mind drifted as Sara started slowly and sensually licking the tip of his cock. The pre-cum originally drooling from the tip of this fantastic cock was now stringing to my girlfriend’s upper lip and tongue as she looked up into the guy’s eyes before slapping his heavy meat on top of her outstretched tongue. 

At that point, I snapped back to reality after becoming distracted by the sexy tongue-slapping scene when it hit me who it might be! When she first started using her dildo Ty, I always wondered how she fit the length of her large dildo so effortlessly into her pussy (more detail on that in another story) and whether she had experienced a large cock in the past. So I asked her, “Is this the cock of one of your ex-boyfriends?”

My girlfriend looked at the camera with a devilish smile and nodded, confirming it was before turning back and taking this mystery ex-boyfriend’s cock very deep into her mouth on the first try. She moaned as her eyes snapped upward, locking onto his off-screen while she deep-throated him, tongue extended to the base of his shaft, attempting to lick the guy’s balls. 

I’d never seen her deep throat any guy like this to date, but it reminded me of a bottle of oral numbing spray she had in her closet toy box at home. When I asked her about the bottle in the past, she admitted one of her ex-boyfriends bought it for her and loved it when she’d deep-throat him using it to remove her gag reflex. Watching her deep-throat her ex-boyfriend as I watched thousands of miles away was incredibly arousing!

At first, if I’m being honest, I was upset inside. However, after the anger converted to lust, I became extremely excited and realized I loved watching it! Once before, when we first started dating, while fixing her computer hard drive, I ran across a video of her and another ex-boyfriend having sex, and at that time, she was embarrassed that I stumbled across it on her computer. Now here she was, openly sucking another ex-boyfriend’s much larger cock live on camera and enjoying sharing it with me! 

For several minutes she sucked his cock like a porn star, looking up towards his eyes while she sucked like a woman possessed. Eventually, she stood up out of view of the camera; the scene focused on their midsections when I heard the sound of kissing as his dark tan hands explored my girlfriend’s ass and pussy. I noticed she wasn’t wearing any underwear when he lifted the elastic material of her dress past her perfect ass to rest bunched up high on her hips. I could tell the guy was fit, judging by his pubic mound, abs, and large thigh muscles. I was mainly focused on his hands squeezing my girlfriend’s bare ass with one hand and playing with her pussy with the other, which, again, made me a bit jealous inside. 

Eventually, she lowered the elastic top of her dress, exposing her breasts before slipping the tiny black dress entirely off. She was now standing completely nude in front of her still-mysterious ex-boyfriend. She turned around, bending forward over the chair she was initially sitting on, as she lifted her left leg closest to the camera onto the cushion, which improved my view of her pussy. At that point, her ex readjusted the laptop screen to make sure I had a great view as he positioned his massive cock head towards my girlfriend’s incredibly welcoming pussy. I heard her say, “Are you watching honey?”

I didn’t answer since I was stroking my cock at full rate again and was laser-focused on the screen as her ex began rubbing the head of his cock up and down her wet and red aroused lips.  I noticed another string of his pre-cum stringing between them when he pulled away, teasing her. 

I knew there was no turning back and was close to protesting. However, no words came out of my mouth as the mystery ex, in slow motion for me, slid his cock deep inside my girlfriend and was quickly pumping in and out of her with full deep strokes. She must have been wanting his cock badly because I could see her juices immediately coating the shaft of his cock, making a wet sloppy sound as they paired.

After several minutes of watching him fuck my girlfriend in this position, I was disappointed when he said he was about to cum. She quickly pulled off his cock while pushing the chair away from her before turning and dropping to her knees in front of him. With an outstretched tongue and eyes locked to his, she accepted the guy’s massive load of thick white cum all over her tongue! At that point, I realized that it must be a trend. Large cocks tend to produce way more cum than I can. 

After he finished, she turned to the camera and showed me the massive amount of cum in her mouth before she swallowed the majority of it, allowing some to drip down her chin onto her breasts as she smiled at me in amusement. She then told me she loved the taste of her ex’s cum and informed me that my surprise wasn’t over. 

Then from the left side of the camera view, another cock fitting the description of Richard’s came into view, and a few seconds after her ex moved his cock out of the frame, another large black cock came into view from the right. I was shocked that she was taking on multiple guys at once and letting me watch live from the other side of the world!

I figured it was Richard on the left because of his well-groomed grey pubic hair, which surrounded a thick white cock. She started by moving everyone back to the bed while her ex moved the laptop to a nearby dresser and pointed it toward the bed to improve my view again. This time, I could see everyone’s entire body except for her ex. My girlfriend was getting prepared at the foot of the bed to suck two of the guy’s cocks, Richard in his late fifties, who I knew, and the other was some unknown black kid she must have just met at the nightclub, I thought since he still had a dress shirt on but no pants or underwear.

I later learned that it was a kid that Richard knew and frequented his sex parties. I heard the rumors of his incredible parties, but I didn’t understand what type of party it was at the time of this story. I assumed it was your typical white summer party that was wild but not sexually wild. Plus, when the kid met her at the club that night, she said his friends bet him he couldn’t pick her up. She learned of the bet from Richard, which played into her desire to make the guy’s night memorable and make his friends jealous. And tick off a line item on her fantasy list of fucking a younger guy.

Story Update December 2024:

I later learned that Sara was the initiator of what I was witnessing. Before they went to the club that night, she told Richard her fantasy of simultaneously experiencing an older guy and a younger guy. Richard made it a reality for her by inviting Jamal to the club to fuck her without her knowledge. Sara invited her ex, initially wanting it to be a threesome between only him and Richard.

Back to the original story:

She looked over at the camera and told me that it was Jamal’s 21st birthday and offered to suck his cock for his present. She then reached out and grabbed his young long soft black cock and started stroking it. The kid was very tall, extremely skinny, and had a ghetto look about him, but he did have a confidence that turned my girlfriend on and an impressive cock that would get any girl rev’d up. At first, his jet-black cock was soft at about 7-8 inches long, which curved downward between his thighs from its mass. Her fingers first wrapped around this kid’s root, attempting to lift his soft shaft horizontally. However, his tip still bent downward beyond her closed hand. 

She started stroking his cock before I witnessed her use her mouth to start sucking his soft cock hard. It took a bit of work on her part to get him hard, but I was shocked when I realized the kid had grown to at least 10-11 inches long and was extremely fat around! A grower, not a shower. I knew this because Sara’s fingers and thumb were not even close to touching while wrapped around his black shaft after he became hard. Richard was shorter in length but just as thick around as Jamal. When my girlfriend proposed we try this fantasy, I had no idea how erotic it would be or that it would happen so quickly. It was extremely hot watching her switch between sucking a much older guy’s white cock to a much younger guy’s massive black cock!

After going back and forth sucking them, her mystery ex-boyfriend came back into the room and walked directly toward the action with his nude brown butt facing me. I couldn’t see directly, but I could tell he had pushed his cock back into the mix as my girlfriend sucked all three guys off at the foot of the bed. It looked like a paint swatch of skin color, ranging from white and brown to black. He kept his back to me, and eventually, I noticed what he was doing with his hands. In his hand, he had a professional camera that looked like his own personal camera, filming my girlfriend taking turns sucking their three impressive cocks. Witnessing this pushed me over the edge, and I came extremely hard again. 

After sucking their cocks for several minutes, she stood, instructing Richard to lie towards the top of the bed. She then got into a doggie-style position with her ass high in the air as she started sucking Richard’s cock. This position allowed the young black stud a perfect opportunity to climb up on the bed and enter her pussy from behind. His cock looked terrific from the side profile, his hand perched high on either cheek of my girlfriend’s ass as he pushed his skinny pelvis forward, sliding deep into her on the first stroke, much like her ex-boyfriend did! I figured her ex just made it easier for Jamal.

My mouth was dry with arousal at what I was witnessing as this cocky young black kid turned toward the laptop camera, flashing a bright white smile followed by an arrogant amused look on his face. He then lifted his arms, flexing like a bodybuilder, clearly trying to taunt me on the other end of the camera, as he slammed his pelvis with quick, deep thrusts into my older girlfriend, making a skin-slapping noise between them from his assault as he grabbed her swinging breasts.

Her ex still had his back to me and still had the camera in his hand filming when he shifted focus from her sucking Richard’s white cock to exclusively focusing on the young black stud fucking her from behind. I couldn’t believe this was happening in real life, and the funny thing was I was so proud of my personal porn star. I couldn’t wait to get home to see her and take her back, and I wanted to involve this black kid again in the bedroom! It was so fucking hot!

After several minutes of Jamal’s assault, he moaned, communicating he was close to cumming when she instructed him to cum inside her. He seemed unsure, probably thinking she was joking. His cock was pulling out slowly when she reached her hand behind her grabbing his forearm, and pulled the kid back deep inside her. He got the hint and quickly followed my girlfriend’s orders, releasing his entire load of cum deep into her womb. The kid initially gripped her waist hard, pulling her ass flush against his pelvis as his body and cock spasmed, and he groaned with his animalistic release. After he started releasing his cum, he immediately pulled about a third of his cock out of her to make room for as much of his cum as possible.

What blew my mind the most as I watched his cock repeatedly spasming as he pumped my girlfriend with his young potent seed was the sight of his cum overflowing her pussy as the excess dripped onto the bed between them. His cock was extremely fat, so it must have been tightly sealing her hole, I thought. I couldn’t believe the amount of hydraulic force I was witnessing from him, and I was very impressed by the volume of cum he produced! I knew his cock must have emptied tons of seed into her womb, and I couldn’t wait to be there in person next time. 

Jamal again looked directly at the laptop screen with his cock still embedded into my girlfriend, when with a crude grin on his face, he quickly pumped his cock forward, forcing even more of his thick cum even deeper into my girl! The look on Sara’s face as this young cocky 21-year-old forced his cum even deeper inside her than any guy before was priceless!

Richard, probably turned on by Jamal cumming, started moaning and released his cum into her mouth as well. I watched as his cum dripped down the side of his cock, out past her mouth. She lifted off his shaft, trying to contain as much of his cum inside her mouth as possible before swallowing what she could of his load. Noticing she let a lot of his cum slip by, she decided to lick up the rest from the base of his cock and balls. Jamal moved to the front of the bed near where she was currently cleaning up Richard, and she took turns cleaning both guy’s cocks at the same time.

She then got off the bed with cum still in her mouth as she walked over to the camera to show me the volume before swallowing it all. She then said, “I love you so much, honey! Thank you for letting me experience this!” 

I responded, “Fuck, babe, that was so hot! I can’t believe you made it happen!”

Amused with my reaction, she looked toward her ex-boyfriend off-camera and said, “See, I told you he was into watching!”

Her ex and everyone in the room seemed amused before he said, “Well, okay then, get that ass over her for round 2!”

Sara laughed at his words, then turned to the camera air, kissing me goodbye while holding her hand to her lips before she signed off. When the call ended, I wondered how many times the guys planned on fucking her that night. I received a text message the following day asking if I had enjoyed my surprise. I told her I loved it, especially Jamal, and added that I’d love to know which ex-boyfriend she was fucking. She said that she wanted to keep it a secret to add to the spice of the situation and that she might want to fuck him again sometime and didn’t want to ruin it. 

I accepted that answer but knew she was friends with all of them, so it’d be hard to tell. I’d probably always wonder, “Is he the one that fucked her?”

When I flew home that Thursday, I told her I wanted to experience it in person the next time and wanted her to let me control and set up the situation. She agreed, and I was excited to make it a reality. I thought, “If I could set up the same situation with Jamal, that would be perfect!” 

Something about watching him cum into her drove me crazy! I couldn’t get it out of my head. I decided I wanted to set up a repeat of the last time she was with Him, so I made it a point to grab Richard’s phone number from her client’s notebook and call him. The events of this story took place in 2012, and yes, she used a physical notebook to track her client’s information and keep actual physical business cards. I helped her organize it at one point so I knew exactly where it was.

When I called Richard late Thursday night, he was initially alarmed when he said, “Hey Jack, I hope you’re okay with what happened the other night! Sara...” 

I wasn’t upset, so I quickly cut him off and assured him I enjoyed it as much as they did. I asked to meet up with him to plan another situation like last week for Sara; however, this time, I wanted to be there and watch. I also told him to keep it a secret from her because I didn’t want her to know I had reached out to him behind her back. 

He agreed and sounded eager to learn what I wanted to set up, so we planned to meet for coffee the following afternoon. He lived in one of California’s most beautiful areas, and we decided to meet at a coffee shop near his house. When I arrived, we acted like what we were meeting for was normal. A passerby would never believe that this older guy, who could pass for my father’s age, fucked my much younger girlfriend only a week prior. Richard and I have met at another party but never maintained communication or exchanged information. He simply knew me as Sara’s boyfriend. 

Over coffee, I said, “Okay, so this is what I’m thinking. I want to repeat what you guys did last week and surprise her with you and Jamal again!”

Richard looked as if deep in thought when he responded, “Doesn’t sound too original, but I understand what you enjoyed about Jamal. The women seem to love that guy. Unfortunately, I think he’s celebrating his anniversary with his girlfriend this weekend.” He sat back in his chair, thinking as he sipped his coffee, and then he continued, “How about you both come by my house tonight? Is that too short notice?” 

Excited that I might see my girlfriend at least fuck him with such short notice, I responded, “Actually, that would work. We have a date night planned tonight anyway, so I’ll change the destination!”

I could tell he was excited to fuck my girlfriend again when he added, “Okay, and I’ll try to invite a friend of mine over to take Jamal’s place.”

He then busted out his phone and searched his photo album before landing on a Hulk-like older white man fucking some young girl in a jacuzzi. He asked, “This is who I’m thinking of. What do you think?” He waited for my response as I took in the arousing image when he continued, “He’s massive too!”

I responded, “You keep photos of your guy friends fucking other girls?” We laughed, and he looked around the coffee shop to ensure nobody was listening to our conversation. Unfortunately, a young barista girl looking directly at our table caught us looking directly at the explicit image he was showing me. With an embarrassed look, she smiled at us and walked past us to clean the subsequent table. I could tell Richard was amused, and we both laughed.

I originally wanted to see Jamal fuck Sara in person, but since he wasn’t in town, this other guy might be perfect. We agreed to meet at 6 pm that evening at his house, and he gave me his home address and instructions for getting past the guard gate, and we went our separate ways. 

As I was driving out of the parking lot, my heart raced. I called Sara on my car phone to let her know that my plans had changed and to be ready for a surprise date night tonight. Later that afternoon, Sara was getting ready and kept attempting to get me to spill the beans on my plans for the evening, but I held firm, only telling her how she should dress very sexy for it. I asked her to wear one of her skimpy, sexy black dresses she wore to clubs that had a zipper down the front and was so tight and thin that her nipples would pop out when cold. I also asked her not to wear any underwear. Once ready, we jumped in the car and drove up PCH. For those not in California, PCH is the Pacific Coast Highway, not The PCH, as some say. In California, we don’t add the word “the” in front of the highway. 

Along the drive, she suspected where we might be going since she’d been to his house before and became increasingly excited the closer we got to his area. I understood just how excited when we passed the guard gate, as she reached over, grabbing and squeezing my cock through my dress slacks, telling me she wanted to suck my cock before we got to Richard’s. She then bent over the center console, unzipping my slacks, and took my hard cock deep into her amazing wet mouth. I pulled over so she could suck me for several minutes until I was close to cumming. I said, “Oh fuck, yeah, babe, like that, I’m so close!”

Unfortunately, with those words, she abruptly stopped sucking my cock and told me to save my cum for later because she wanted it in her pussy. I continued our drive to Richard’s large mansion but was feeling frustrated I didn’t cum. When we finally arrived, I turned off the engine, looking toward Sara, attempting to gauge her reaction. She had a tremendous, excited, happy grin with glossy eyes, communicating how much she loved me. We exited our car and were immediately hit by music playing in what seemed like his backyard. We walked through an open door into his foyer when Richard greeted us in the hallway, welcoming us to his party. 

I was confused when I witnessed a group of beautiful people partying in his backyard around his pool! It was a warm, beautiful afternoon, and the sun was starting to descend toward the ocean as I took in the scene. Most guys wore polos and looked professional, while the others were in board shorts talking with girls dressed in their bikinis. I thought, “Perhaps one of them was the guy he had in mind. Perhaps once the party dies down, we’ll seduce Sara!”

The group consisted of ten older guy friends of his and four incredibly sexy wives or girlfriends. I didn’t figure out their status, but I figured the girls would be paired with one of the guys present in some way. Two of them were young-looking, probably in their mid-twenties. It’s typical in our area for younger girls to date much older, wealthy guys, especially after the guy gets a divorce. From a young guy’s perspective, I must be honest and express how annoying it is. But I’ll be old someday, also. The two older women were also stunning, probably in their early thirties, closer to Sara’s and my age. 

All the women looked like models together dressed in skimpy, sexy bikinis, except for my girlfriend. Several minutes passed when Sara and I split up so I could use the restroom. When I came back outside, I noticed my girlfriend was having an in-depth conversation with a couple on the other side of the pool deck, with Richard standing by her side, holding her as if she were his girl. At that moment, jealousy started growing inside me as I walked toward them. I would have continued my journey but was interrupted by a couple who greeted me, saying, “My husband and I are glad you and your girlfriend joined our group!” The girl had a gorgeous smile and eyes as she distracted me when she continued, “How long have you guys been swingers?”

I thought I heard the girl wrong when I said, “Excuse me?” She smiled and repeated, “How long have you been swingers?” I was in shock and didn’t answer her question as I apologized and excused myself to rejoin Sara as my mind realized what Richard had done. I was pissed, thinking, “That’s not what we discussed!” 

Sara noticed my upset look as I approached them. She grabbed my arm and said, “Babe, are you okay?” I didn’t respond; concern crossed her face as she continued, “Babe, thank you for setting this up for me! I knew you were freaky, but damn, honey! A swinger party? God, I love you!”

She kissed me on the cheek and squeezed my ass, which disarmed me, but I still wanted to pull Richard to the side to have a word. Sara’s large grin and energy told me she was excited to be at a swinger party and wanted to participate! The fact that we were among ten much older men and four sexy women didn’t bother her. Richard then said, “Okay, let’s get this party started! Shall we all jump in the pool?” 

Sara and I didn’t bring bathing suits, but Richard knew that since he hadn’t told me about his plan in the first place. My plan wasn’t exciting enough, apparently. He then guided Sara upstairs, leading her by the hand to pick a bathing suit, and told me I could borrow one of his. 

When we started walking up the stairs, Sara was ahead of me when Richard guided her to a nearby bedroom to pick out a suit and told me to follow him to his room for my suit. When we finally entered his room, I whispered angrily, “What the hell? You should have told me you invited us to a swinger’s party! What the fuck! Is that guy even here?”

Richard gripped my shoulder, saying, “Yeah, I was going to tell you, but I didn’t want to make you uncomfortable. I knew Sara wouldn’t mind, but I wasn’t sure if you’d be down or not. If you feel uncomfortable, please let me know.” He paused as if deep in thought when he continued, “Man, I didn’t mean to...”

That’s when Sara must have realized we were taking a long time and interrupted our whispering as she walked into his bedroom with her signature sexy smile, saying, “Is everything okay, boys?”

We acted as if nothing was happening and went down the hallway to the bedroom, where a very skimpy selection of bikinis lined a bed. One of the men at the party owned the swimsuit line. It was a collection of the skimpiest bikinis I’ve ever seen. Sara did what I expected and chose a white suit that would barely contain her large breasts and a skimpy side-tied thong bottom that I knew wouldn’t cover much of her pussy. 

I could tell the suits were explicitly selected to limit her selection to only thin and tiny bikinis, and the one she selected would leave little to the imagination. I also knew she looked forward to giving all the guys and girls downstairs a significant thrill. My cock started to stir as my girlfriend stripped completely nude in front of Richard and me in the middle of the bedroom.

Richard and I both watched her from either side as she adjusted her suit top and bottom. She then turned toward us to model the suit for us, and we could see the outline of her hard nipples through the thin material. I then said, “Damn, babe, you look so sexy in that!” 

She loved my comment before turning to check herself in a nearby full-length mirror. After seeing herself in the mirror, she decided to tease us even more by lifting each triangle covering each breast and then pinching her nipples to make them even harder. She then turned back to us and asked in a sexy voice, “What do you boys think? To risqué?”. I was silent, taking in her beauty as Richard answered, saying, “You look amazing! The guys will love seeing you in that!” 

After saying this, my girlfriend walked directly up to him, reaching her hands around his neck as she started making out with him in front of me. The guy didn’t care that I was present in the room as he dropped his large hands, which cupped each of my girlfriend’s ass cheeks as they kissed passionately like lovers. She then turned to me and did the same, this time with Richard watching. 

He eventually closed the distance behind her when his hands reached around my girlfriend’s midsection. He openly grabbed her large breast between us as he ground his pelvis into her from behind and kissed her neck. 

We stopped our affection pretty quickly when Sara decided we should rejoin the party. By this point, all the guys joined the girls, wearing swimsuits and spreading out in the Jacuzzi or the pool, drinking their cocktails. Richard and Sara were in front of me as we exited the house. I was planning on following her into the pool when Richard walked to his left, heading toward the Jacuzzi, and Sara turned toward me, pushing against my chest to stop me in my tracks, turning to whisper in my ear, “Why don’t you watch me flirt from the Jacuzzi with Richard?”

I got the hint that she wanted to be hit on alone in the pool, so I changed my destination to the Jacuzzi, as she had requested. From my vantage point, I could see my girlfriend’s sexy bikini-clad body entering the pool slowly as the much older guys openly stared at her body and started flirting with her immediately. One guy, in particular, stood out since it seemed like she knew him somehow as she gave this very tall, muscular guy a loving hug as he lifted her from the water. Her arms wrapped around his neck like they were with Richard and me moments before. She knew him, and he looked a lot like the big guy in Richard’s photo from the coffee shop, but I wasn’t sure.

As the night went on and the alcohol flowed, I could tell she was getting more flirtatious with the men and started hanging on some more than others. At one point, I noticed her on the shoulders of that tall guy she had embraced early on, whom I hadn’t been introduced to yet. She occasionally looked over to ensure I was watching her flirt and then turned back to focus on the guys before her. Richard pointedly introduced me to the two younger women in the Jacuzzi, and I wondered if Sara was jealous or watching me flirt in return.

At one point, one of the women in the pool decided to make the first sexual move of the night and playfully removed one of the other girl’s bikini tops from behind. They laughed, splashing, and then it was like a chain reaction.

One of the other girls took that as an opening and reached from behind Sara’s back as she was talking with the handsome guy in front of her, a nearly fifty-year-old hulk of a guy, pulling my girlfriend’s bikini over her head, fully exposing her large breasts to the hulk in front of her. She didn’t rush to cover herself up but instead pushed her breasts together in an inviting way to the man with a naughty smile on her face.

He then leaned down, reaching his massive arm around her waist as he took one of Sara’s breasts into his mouth. His other hulking hand reached behind her, squeezing and rubbing my girlfriend’s thong-covered ass. They were on the day beach side of the pool so that I could see it all. Sara’s head and eyes turned to lock with mine, and I could tell she was amused to have me there watching her as she got groped by this guy who was a stranger to me. It was incredibly erotic to see a man much older than my girlfriend take control of her body like that. I didn’t realize it immediately, but Sara had slowly reached her right hand out, slipping it into the guy’s board shorts, and was now openly stroking his hardening cock in the water in front of everyone.

At this point, nobody had left the party, which meant there was a strong possibility all ten guys might take their turn fucking Sara! The other men took notice and started lowering their swim shorts as the other two women our age sunk to their knees and sucked their amazing cocks.

At that point, I noticed that the two younger women in the Jacuzzi had also lost their bikinis, and the men around me lifted their naked bodies out of the water and sat on the edge of the Jacuzzi. Richard grabbed my shoulder and said, “Don’t worry about Sara. She’s enjoying herself. You should as well.”

One of the girls at that moment came up to me, grabbed the hem of my board shorts, and started pulling them down, exposing my cock as she began stroking me in the space between us. At this point, I lost track of Sara since I was distracted, and I wondered how she felt about me hooking up with other women and if she’d care. We haven’t discussed the other direction. The young girl dropped to her knees in the Jacuzzi as I sat on the edge like the other guys were, and the girl started sucking my cock. She looked incredible, making perfect eye contact with me before smiling and moving on to Richard’s older cock next to me. I immediately needed to find Sara again to see what she was doing.

As I exited the Jacuzzi, I noticed the group had split up. Where two older guys stayed in the Jacuzzi with the two younger girls, Richard left with the other two girls our age, walking toward his bedroom, and my girlfriend and several men were nowhere to be found. At least not outside. I stepped inside a long open section of his house, with large glass windows that slid entirely out of the way, creating an indoor-outdoor feel to the living room. That’s when I saw her lying on her back over a coffee table with a group of eight men ranging from 40-60. Two of the men were sucking on my girlfriend’s large naked thirty-two-year-old breasts, while another was between her legs eating her pussy, while another had his cock in her right hand as she stroked him toward her open mouth from above as he stood over her head.

She had this older white guy’s cock with a bulbous red tip nestled between her lips as she used her hand to stroke his full length downward toward her mouth. The guy’s cocks ranged from 7-10 inches, and I figured they were explicitly invited to his party because of their size. Two guys seemed a little larger than me, but all were incredibly thick. 

I didn’t imagine it’d get to this point, but Sara’s behavior turned me on, and I loved what I saw. She was so fucking hot! I decided to sit on another couch nearby and watch her enjoy herself. She eventually noticed my presence in the room, and I noticed that the man’s cock in her mouth was the one whose wife asked me when we started swinging. Our eyes met, and a smile crossed his face, knowing that it was my girlfriend sucking his old cock at that moment. 

Sara eventually paused, sucking his cock, and switched to the guy on her left when she made eye contact with me. I could tell the level of pleasure in her eyes as she was sucking this other older guy’s cock directly in front of her younger twenty-nine-year-old boyfriend. All the men took great care of themselves and seemed to have no issue getting their cocks hard for my girlfriend. 

I’m sure the Viagra and a few cock rings helped some of the men out. I could tell she loved the attention of all the older men and especially loved being gang-banged by men twice her age while her boyfriend watched nearby. We discussed the idea briefly about a gang-bang but never thought it was a thing she would ever try in real life. Threesomes, sure, but a full-on gang-bang was beyond my imagination.

To be clear, I didn’t think Richard would invite so many guys in the first place, but I wasn’t complaining now either; I was loving it! Sara must have believed by this point that I wanted her to get gang banged because she was still under the impression that I had set up this evening’s event for her. Richard and I never corrected that narrative. 

Eventually, she took control of the guys around her and called out to one of the men watching, standing in an alcove out of my view. My girlfriend used her finger to call the man over, communicating that she wanted his cock inside her first. The hulk of a guy from the pool stepped into the room from a nearby hallway with his massive cock finally exposed to my view, and it looked amazing! It looked a lot like Ryan’s cock, one of her favorite cocks to date, only this time it was attached to some large, muscular, late fifty-year-old man. When I say large, you could tell the guy was a meathead who hit the gym often. He was also the tallest of the bunch, approximately 6 foot 5 inches, and stuck out as the alpha.

His cock was exactly the size she liked, and I loved watching from the sidelines as the guy lined up between my girlfriend’s spread legs before slowly rubbing the tip of his cock against her pussy. Before he continued, one of his buddies handed him a condom, and he put it on. I then heard my girlfriend’s cute voice beg for him to fuck her as he slowly pushed his impressive cock into her pussy. 

She moaned loud with pleasure, and I could tell he was hitting all the right spots with his years of experience as he buried his fat cock to the hilt inside her. It seemed like it was just the two of them at that moment, and I knew she had found her next lover after Ryan and James. His cock looked so good going in and out of her.

Story Update December 2024:

I later learned the guy paying the most attention to Sara was Richard’s friend who fucked her on his boat. The captain/neighbor. At this point, Captain didn’t know I was her boyfriend.

Back to the original story:

After the guy fucked her lying on the coffee table for a few minutes, he changed position as the hulking guy moved to the nearby couch to be seated opposite me before Sara mounted him again, riding his cock reverse cowgirl. She put her feet up on the couch cushions directly behind his thy muscles, and I watched from the front as his massive cock disappeared inside my girl over and over with her legs spread wide. In that position, I made direct eye contact again with Sara. Another guy stood on her side as she sucked his cock. Seeing my young hot girlfriend in this position turned me on so much I decided to walk over, stand on the couch, and present my cock to get sucked by Sara while she alternated between me and the other guy.

I swapped positions with another guy who was much larger than me and moved back to the couch opposite the coffee table to watch. As I sat back down, I loved the scene of Sara bouncing up and down, fully taking this meathead’s fat white cock!

Eventually, Sara switched to riding captain cowgirl, and another two guys lined their cock over the back of the couch for her to suck. I found it funny that she stuck to fucking the Captain, and I wondered why.  Captain eventually leaned forward, grabbing Sara and lifting her back to fucking her on the coffee table in the middle of the couches.

I could tell he was trying to hold himself back from cumming when Sara leaned up, whispering something extensive into his ear before he looked over at me. The large guy lifted off my girlfriend’s small frame when Sara and my eyes met. I loved the level of lust in her eyes when we both shifted our gaze back at the guy as he removed his condom from his shaft. I was disappointed that the guy seemed to be switching to let another guy take his turn. 

I was wrong and a little shocked when the guy slid his engorged unprotected 10-inch fat slab of meat back deep into my girlfriend’s young pussy. After fully burying himself again, the guy looked over at me, making eye contact again. I thought, “Did she tell him I’m her boyfriend?”

He seemed to get a second wind by pausing because he fucked her with even more passion as she took care of two other well-endowed guys standing on either side of her. The excitement drew me closer to the action as I stroked my cock, watching from above as his body tensed up, and I watched him pull his large cock almost entirely out of her, leaving only his large cock head inside. His shaft jumped as he throbbed, and I knew he was depositing a sizable load. Sara and my eyes met again as I watched over the guy’s shoulder as he was cumming into my girlfriend.

When he finished, I thought he’d pull out and see a river of his cum pouring out, but the guy surprised me again and instead quickly pumped his cock shaft balls deep inside her holding himself deep like the black guy did last week. They were part of the same swinger group, so perhaps the black kid picked up the move from him. I could tell by his actions that he intended to breed my girlfriend. Pulling his cock mostly out as he came left a void for his cum to fill, and due to the guy’s girth, being one of the fattest cocks I’ve seen after the black kid, he must have forced all of that cum deep into Sara’s womb when his piston pushed forward. 

Another detail I noticed as he did so was her belly and pubic mound rising as his shaft was buried to the hilt without a drop of his cum leaking by, unlike with Jamal. After several seconds of him holding his cock deep in my young girlfriend’s pussy, Sara, and my eyes darting between the three of us, he slowly started to pull out. I watched as his cum slowly started dripping out of her, then a few seconds later, even more streams of cum came flowing out of her as she sat up, using a finger to coax some out of her depths. I was shocked at the amount of cum that eventually was pushed out. Again, this is the first time she allowed me to be in the room when she fucked someone else. Every time prior, she enjoyed sending me texts and videos of her actions or letting me listen over the phone.

Sara stood as another older guy grabbed her hand, guiding her to a nearby bedroom. As she left the room, Sara said, “Babe, have fun. I’ll see you later. I’m sure the girls outside would love to do more than just suck your cock. Go!”

With that comment, the group of guys realized, at the same time, with amusement, that I was her boyfriend and sharing her. The big guy I was calling Captain was standing completely nude in front of me and didn’t say a word as he turned to head back outside.

As she entered the room with the remaining seven guys, one of them closed the door behind them, grinning at me. At that point, Richard must have overheard our conversation when he called to me from the banister, and I joined him and the two girls he was fucking up in his room. We ended up staying the night at his house that night, and I listened from the guest room as several guys took turns sharing my girlfriend, fucking her all night long. When I woke up, Sara was not in bed with me, so I left the room to search for her.

I heard a shower running down a long hallway when I came across her showering with Richard. He was the only guy I knew left at the house, and I loved watching them shower together. She was soaping up his cock as I entered the large room, which was still rock hard, probably from too much Viagra.

My presence was immediately noticed, and he offered to join them. I declined and said I’d wait outside on the deck for them to finish.

Richard emerged from the shower in a robe and said, “Hey, I’m sorry I didn’t tell you in advance that this was a swinger’s party. I just really wanted you guys to come. You guys are always welcome in the future.” We stood there silent, both in thought, when he continued, “I hope you’re okay.”

I thought about what happened and responded, saying, “Actually, I’m shocked that I was okay with Sara getting gang-banged like that. Was hot!”

Sara eventually left the bathroom still stark naked before handing me her phone, asking me to photograph her sucking Richard’s cock again before we left. The bright sun backlit her perfectly, and it’s still one of my favorite shots of Richard unloading all over her large breasts. The censored photo is in her album.

I’ve now learned the captain/neighbor’s name, and it’s John, so I’m sure Richard, John, Ryan, James, and hopefully Jamal will be our new group of regulars to fuck Sara, and I love the variety!! I still haven’t seen her fuck a black guy in person, but I guess that’ll have to wait. That night Sara fucked all ten guys at the party, both including Richard, and joined his parties without me many times after that.