A Pervert's Journey Pt. 8

**I'm not sure how readable my story is, but I get some pleasure thinking back on some of my adventures. This story is 100% true with some minor details being changed. I'll try to include something sexy in every part, but the general plot is a slow drip transformation from a young inexperienced boy into a bisexual cuckold man, documenting the romance that sparked it and its ultimate betrayal. As a fair warning, there are a large amount of themes explored along the way to varying degrees: CNC/Rape, Anal, Incest, Drunk/Drugged Sex, Group Sex, Gay/Bi/Lesbian sex, Cuckoldry, SPH, minor watersports, and more.**

[Planning Our First Threesome](https://www.reddit.com/user/SnBStrategist/comments/1rmh2ts/a_perverts_journey_pt_7/)

Bonnie and I sat in the station wagon in silence while parked outside our favorite motel. I’ll never forget feeling this completely new mix of emotions. I was oscillating between a state of intense fear and excitement. At any moment it felt as if I’d throw up. 

“Are you sure you want to do this, Billy? We don’t have to.” I looked over at Bonnie all dolled up in her makeup, her eyes glassy from her own heightened state. After a week of scouring craigslist, we had finally settled on a random stranger for our threesome. The entire process was handled with the utmost of delicacy. I could tell Bonnie was doing her best to protect my ego and make me at ease. We probably received well over 200 emails. Unsurprising considering how hot Bonnie is. It wasn’t lost on me that every single candidate she wanted to reach back out to had perfectly average sized dicks. Believe me, there were plenty of monsters offering their services. I’d covertly analyze Bonnie’s reaction to them, but she practiced perfect stoicism. If she were interested in the big dicks, she surely didn’t show it. 

I grabbed her hand and gave it a squeeze. “I do. I’m excited, I think. Maybe just nervous.” Part of me was terrified. What if this guy was a killer? Could I take him in a fight? I’m literally opening the door for a stranger to come in and help me fuck my girl. Am I insane? The time for second thoughts passed though. The stranger’s car pulled up beside ours. As planned, we went into the room first. A few minutes later the knock at the door caused both of us to involuntarily jump. 

Our third wheel for the evening was named Brian. He was short, about the same height as me, but had a far more athletic build. He had short sandy colored hair, and was probably in his early 30’s. He sent us a single nude. Despite Bonnie’s best efforts, I was still self-conscious. But that wasn’t her or Brian’s fault, I had to just get over it. We could have weeded through another 200 applications and I still would have felt this way. I also started to feel weird after spending so many hours looking at pictures of naked men, so I finally gave up hope of us finding a small dicked guy and agreed to Brian. He had a nice body, muscles that I lacked. And while Bonnie weeded out the big dicked applicants, Brian’s girthy 6 inches was still more than my 4. 

He shook my hand on his way in, and gave Bonnie a brief hug hello. He was nice in his emails and in person, but there was an undeniable confidence or smugness about him. It made me wonder what he thought of me allowing this to happen. We sat awkwardly in a circle. Us at the foot of the bed, and Brian on one of the chairs. 

“So what made you guys want to invite another guy to bed? I gotta give you credit Billy, I’d have a hard time sharing a girl as hot as Bonnie.” Bonnie took my hand in hers and gave it a squeeze. 

“Well as you might imagine, Bonnie is a lot to handle. She has quite the sexual appetite. And well, we had a threesome with one of her female friends. So I thought why not even the score a little bit and let her have fun.” 

“Damn…good man.” 

“Have you done this before with another couple?” Bonnie spoke up softly. Her squeaky voice revealed how nervous she was. 

“Yea a few times. I’m a photographer by trade, so I actually started doing this a few years back when a client hired me to take some shots for her husband. One thing led to another and they invited me back to their place.”

“Wow,” Bonnie whispered dreamily. 

“If you guys want me to take some sexy shots of Bonnie or the two of you, I’m always game!” Bonnie vigorously shook her head. Her shyness was a new look. “No pressure then. Not everyone likes being in front of the lens. I bet you’d look great, though.” I could feel Bonnie’s breaths deepen. “So what exactly do you want my role to be in all of this? How should it go down, any ground rules?” 

Bonnie turned to me expectantly, clearly incapable of articulating complex thoughts at the moment. “Yea, so…obviously no touching between you and I. The goal is to focus on Bonnie and give her a good time. Our only ground rules are no kissing on the lips, and you have to wear a condom.” 

“Sounds good to me, man!” He leaned in and gave my knee a little slap. For a moment, silence hung in the air and Brian understood how new this whole situation was to us. Thankfully he took the lead. “How about this, I sit here on the chair. And you guys go up on the bed and start without me. I’ll direct you like I’m doing a photoshoot without the camera. That might help with first time jitters, right?”

Bonnie and I crawled to the top of the bed and laid next to each other. Bonnie was wearing these hip hugger jeans that drove me crazy, with a frilly flowery top that stopped just short of her belly button, her hair was tied up in two buns. She looked like this delicate little hippy nymph. I placed my hand on her abdomen and she shivered. We closed our eyes and shared a long, intimate kiss. For a moment it was just her and me, and my nerves began to subside. Then a low voice from the corner of the room commanded us into action. 

“That top is such a tease. Billy, why don’t you reveal a bit more for me.” His request caused a rush of blood to my dick. My hand crept further up Bonnie’s abdomen, pulling her top with it, revealing a rose pink bralet. I flipped it off revealing those tiny puffy nipples that I so adored. “Bonnie, your body is out of this world. I actually prefer itty bitties.”

In her adorable little girl voice, Bonnie thanked Brian for his compliment. I lowered my mouth to her tits and began nursing on them, while Bonnie stared at Brian sitting across the room. “Let’s keep the show rolling Billy. Those pants need to come off next.” On command, my kisses trailed from her tits, down across her navel, stopping just above her pantline. I peeled her jeans off. They were so tight that they were taking her thong with them, so in one swift motion Bonnie laid there completely naked before me and a man we had just met. Brian let out a whistle. 

I resumed kissing lower now, soft coos and moans escaped Bonnie’s lips as I softly made out with her pussy. Bonnie broke her silence, snapping me out of my trance. 

“You have a very nice dick, Brian.” My head spun around to see Brian was just in his shirt now, his fat 6 inches proudly standing at attention while his fist glided up and down its length. 

“Thanks Bonnie. Any ideas on what you’d like to do with it?” Bonnie bit her lip and nodded. “Billy, why don’t you join the party?” The idea of getting naked in front of another man swiftly took me out of my aroused state. Wordlessly I stripped down, my 4 inch hard on slowly softening as I presented it to the room. Bonnie realized as much and immediately wrapped her delicate fingers around it, helping me keep form. With her other hand she pulled her face to mine and looked me in the eyes.

“It’s just you and me, Billy.” Her words of encouragement reduced my anxiety. We began making out, but despite Bonnie’s best efforts with her hand I continued to lose my hardness. 

“Bonnie, use that sexy little mouth and help Billy out.” Brian barked from across the room. I laid on my back while Bonnie began sucking my dick while on all fours, her back arched as she presented her ass and pussy for Brian to see, which he wasted no time acknowledging. “Fuck that looks so hot.” We locked eyes from across the room. I couldn’t help my gaze from falling to his dick, his fist pumping slightly faster as if to put a show on for me. I looked up to see Brian flashing a grin back at me. Bonnie easily deepthroated my full length, the sensation causing me to throw my head back in pleasure.

With my eyes closed, I felt the weight distribution of the bed change, followed by a slow and sexy moan from Bonnie. When I opened them, Brian was now on his knees behind Bonnie. His hand fluttered between her legs as he played with her pussy. It was the dirtiest thing I had ever witnessed. Part of me found it so hot, but almost immediately my dick went limp in her mouth. She did her best to suck it back to life, but it was no use. She looked up at me with questioning eyes, wondering what to do. 

“I’m having a little bit of stage fright here. Bonnie, why don’t you suck Brian’s dick for a bit while I get hard?” 

“Are you sure?” I nodded assuringly. I took Brian’s spot kneeling at the foot of the bed. Brian walked on his knees towards Bonnie, his dick bouncing triumphantly. With the cockiest grin I’ve ever seen, he asked Bonnie to help him with his shirt. My knees went weak when Bonnie quietly obeyed. Her nails softly grazed his ass cheeks before taking the bottom of his shirt and lifting it up over his head. They were inches from one another, Bonnie’s eyes examining his now fully naked form up and down. “You have a really nice body, Brian. I like your muscles.” 

Involuntarily my dick twitched, luckily I don’t think either of them noticed. In a trance and without further words exchanged, Bonnie dropped to her hands and knees and began to eagerly suck Brian’s dick. Almost immediately I realized how much more difficulty she was having taking his full length with her dainty little mouth. In my mind I thought the 2 inch difference wouldn’t matter as much, but apparently his girth made it a difficult task.

Brian gave her ass a little smack, causing a muffled and surprised moan to escape Bonnie’s lips. Hearing her groan while gagging on Brian’s dick helped me get fully hard again, so I took the opportunity to get behind Bonnie. With both hands on her hips, I aimed my dick at her entrance and effortlessly slid into her sopping wet cunt. 

Brian gave me a fist bump and a, “Hell yea man,” welcoming me back to the threesome. He took a fistfull of Bonnie’s short black hair, and began holding her head in place while he rocked his hips back and forth to fuck her mouth. Bonnie was gagging, making a gargling sound as she struggled to breath through her nose. She didn’t seem to mind being face fucked, as she began to push back harder on my dick. After spit roasting her for a few, Bonnie came up for air. 

“Let’s switch! My jaw is starting to hurt a bit from Brian’s dick.” It was implied that she wasn’t used to a dick bigger than mine. She did her best to word it thoughtfully, but my self-consciousness started to creep back into focus. We flipped positions, but I laid on my back to give Bonnie’s neck a more comfortable angle. She immediately began fully swallowing my dick in long strokes in and out, having a much easier time. Brian finished putting on his condom. He gave Bonnie another spank on the ass, causing her to jolt up with a smile and look back at him. 

“Hey!” She playfully scolded him. 

“Sorry, but it’s very spankable.” They maintained eye contact as he entered her. 

A thoughtful little “Oh!” escaped Bonnie’s lips, followed by a deep and breathy groan as his dick bottomed out in her. Bonnie looked up at me, “Baby, he’s fucking me.” She went back to my dick, but struggled to keep her mouth on it as Brian picked up his pace. I knew it was only a matter of time before I’d start to soften again, I tried to close my eyes and ignore him fucking her. But it wasn’t long before my limp dick was left ignored while Brian brought Bonnie to her first orgasm of the evening. When she recovered she realized my predicament. “I’m sorry Billy!” I shook my head and asked to make out, thinking it might help. 

Brian moaned, spreading both of her cheeks while he continued fucking her from behind. “Fuck Bonnie you’re so tight.” Bonnie’s eyes rolled to the back of her head.

 “He’s fucking me so good baby,” she moaned in between kisses. Her talking always got me hard, and this time was no different. Hard again, Bonnie attempted to go back to sucking me, but I quickly lost my erection. I was having a great time, but this was admittedly frustrating. 

“Bon, maybe I just watch for a minute and try to rub myself hard again.” Bonnie looked slightly confused, wondering if I was upset. I acted as nonchalant as I could, telling her not to worry about it while sitting at the foot of the bed so that Brian and Bonnie could continue. Bonnie laid on her back and spread her legs. She looked like a goddess  as she invited another man into her sacred place. Her pussy shined in the lit room from how wet she was.

Brian slid into Bonnie in missionary and she sighed happily. I slowly massaged my dick to the sight, eventually getting it hard again. Bonnie was watching me intently, and beckoned me over with her finger once I was ready. God bless her for trying, but the moment I got back to her face, the proximity to Brian’s hulking mass over her caused me to immediately lose my erection again. I reassured her I was fine, and that it might just not happen for me tonight. She looked concerned. 

“Really it’s fine, I can get hard watching though so just enjoy.” I returned to the foot of the bed. Brian began kissing Bonnie’s neck which caused her to coo at first. He got higher and higher though, causing her to look away from him awkwardly since we clearly told him no kissing on the lips. He responded by pinning the full weight of his body onto hers, both of his arms went above her head, and he began long powerful strokes that caused Bonnie to yelp each time his pelvis made contact with hers. With her face turned away from his hungry mouth, she wrapped her arm around his large bicep, taking a deep inhale of Brian’s skin while kissing his arm in ecstasy. 

The erotic sight of her worshipping his muscled arm while he punched her pussy with his thick dick turned me on in a way that could only be described as an out of body experience. Finally my performance anxiety faded away as I vigorously jacked off. By now, Bonnie was so lost in the moment that she barely looked my way. Brian grabbed both of her legs with his powerful arms and put them over his shoulders, and began fucking her almost angrily. The entire time he continued kissing and biting at her neck, trying but failing to get her to give up and kiss him. Bonnie’s moans got louder, bordering on screams at this point. She abruptly stopped and then there was silence save for the sloshing of her pussy followed by a new sound altogether. 

Goosebumps ran down my spine as Bonnie’s whole body shook like something out of an Exorcist movie, her pussy spouting a deluge of wetness. She was squirting for the first time. Something I had never witnessed, or knew she could even do. Her orgasm drenched the mattress, and sparked both Brian and I to cum along with her. Brian slammed himself to the brim, unloading into the condom. I looked down at my cum on the carpet, inwardly thankful that Brian orgasmed at the same time as me to avoid vicious post nut clarity. 

I looked down at my cum on the carpet, and then back up at Bonnie. Her arm was still wrapped around Brian’s bicep in an embrace, but she was panting heavily and staring back at me with wide eyes. She didn’t know she could squirt either, her face revealing an expression that could only be described as, “Holy shit.”