I woke up earlier than expected.
The previous night was a wild one. I didn't expect much sleep, given the gauntlet of events, thoughts, and emotions that had occurred.
First, meeting up with David earlier in the evening and having a nice fuck with him that opened up a few new doors. David had set up a dildo with a suction cup on the wall of his shower, and took me in to make a choice. I ultimately decided that he wanted David to fuck me while I sucked the dildo, giving me a first experience of what a spitroast would be like. I truly thought it was insanely hot, and I'm absolutely down for trying it with another real cock sometime. Then, David took me to his bedroom and had me ride his dick while he laid in his bed, which resulted in me shooting a load of cum with a dick inside me for the first time ever. It was so unexpected, yet it was incredible. David's dick was hitting me just right I guess. Ending our fuck session with a FaceTime call to Jeff, allowing him to jerk off in his hotel room while watching David fuck me while I suck on the dildo again was the best part though. Not only was I taking on two dicks at once, but I was putting on a show for the man who first got to fuck me. I enjoyed being watched, but really enjoyed watching Jeff stroke his cock in response to me getting fucked. We ended our session with David shooting a thick load of cum down my throat.
When I got home, I got a very unexpected surprise from my girlfriend Kayla. It was a nude picture of her best friend, Katie's fantastic ass as she laid passed out in the hotel room bed from what I thought was a night of drinking. After some talking, Kayla dropped a bombshell on me, and told me that her and Katie went shopping together for sex toys, and used them on each other, resulting in both of them fucking the other with a strap on. As if that wasn't surprising enough, Kayla told me that they planned on doing it again. After a near nervous breakdown on her part, I brought up that she might be bisexual, and in order to calm her down, I came out to her and told her I was bisexual. She finally admitted it to not just me, but herself and she also came out as bisexual. We decided that when Kayla got back in town, we would get together and talk things out, and figure out if we were going to remain a couple or break up.
Having had a lot on my mind in regards to Kayla and I, I knew it wouldn't be a surprise to me that I wasn't able to go to sleep. I needed something to help clear my mind of things, even if it was just for the night. The idea came to my mind and I went with it...I needed fucked again by another man. Jeff wasn't an option for me, as he was out of town. David had told me that once he gets off, he's done. I needed another option, so I checked my email and texts, trying to think of something. Then, I found an email from an older guy named Tim. He posted on Craigslist looking for a blowjob and I responded to it. He emailed me back while I was busy being used by David, and said he wanted to chat. He included a phone number to text. I text him and realized that he had only recently sent the email. Even though I didn't expect an answer that late at night, Tim text me back. He invited me over to chat, so I went over, prepared for just talking.
Tim invited me to sit down with him on his porch and then proceeded to basically conduct a job interview. Asked me questions about how many guys I've been with, what all was done, if they came, and if so, where did they cum. After a few minutes of back and forth, he invited me inside for what would be my best man-on-man sex yet. Things were going well, as I gave him oral, then he invited me upstairs to his bedroom, where he started getting a little more dominant and he face fucked me on his bed. Before he did so, I noticed his work shirt had the same logo of the company that Kayla works for. Turns out, he was a security guard there the night, and he knew Kayla. He remembered seeing my picture at her desk and put it together that I'm her boyfriend. He gave me his word that my secret was safe with him, so we continued.
Being the vocal one during any sexual activity as I discovered he was, he was talking often, mostly some dirty talk, but then he brought up Kayla and told me how lucky I was. Started talking about how good she looked, how nice she was...then he said "and she sucks dick like a champ." and I snapped. I demanded answers from him, and long story short, he did something pretty major for her apparently shortly after they met at work and she decided she owed him big time. I wasn't in the picture for a few years yet, so I made peace with the fact that Kayla gave head to her older co-worker. This was when Tim got more dominant.
He made me strip down out of my clothes and go put on a thong Kayla had gifted him early on in their encounters, and then he handcuffed me. He became fully in charge of what would happen. And then, he told me exactly what his plans were.
"I'm going to breed you. I might not be the first dick in that ass, but I'm going to be the first one to spread its seed. You're going home with my cum running out of your asshole tonight." he said. And, he was a man of his word.
As he was fucking me bareback, preparing to blast a load of cum directly into my ass, he told me about how on their last time together, he not only took Kayla's virginity, but also was the first one to fuck her in the ass. As I had to listen and get worked up, his dick was hitting me just right, much like David's earlier in the night, and for the second time that night, I shot my load with another man's dick inside of me. Tim, being the dominant one he was for the night, decided to "punish" me for experiencing any pleasure in all of this. He scooped my cum into his hand, had me open my mouth, wiped my own cum onto my tongue, then shoved his cock... which was literally just in my ass...in my mouth and back to my throat, pushing the pool of my own cum off my tongue and back down directly into my throat, then briefly fucked my mouth, adding ass-to-mouth to my resume too. After all that, he uncuffed me, had me lay down flat, and he pounded down into my ass like a jackhammer, until he finally reached his climax and shot a huge load of old man cum into my asshole.
As aggressive as he was, as intense and unexpected as the night turned out to be, Tim immediately turned into my favorite fuck buddy. I already knew that I would come back for more, but then he offered a proposition.
Turned out, other than his sexual experience with Kayla, he had considered her a friend, and he had picked up on a few things from her. Not only did she truly care about me and want to make things work out for us, but she had also been hoping for a ring. At his urging, I decided that our relationship was absolutely worth fighting for, and I would need to get her an engagement ring sooner rather than later. He proposed to take a line of credit he had in his name, and use it to buy her a ring, and he'd keep it safe. I would pay him visits, and we'd have fuck sessions, and based on what happens, Tim would credit me so much towards the ring. I would work it off.
I accepted his offer and ordered a $3000 ring. He gave me a $500 credit for our first meeting, so I knew a bar had been set. I would visit him again soon and earn more credit.
After one hell of a night, I finally got to sleep around 3am. I expected to sleep the day away, but when I woke up at 9:30am, I knew something about this day was going to be great. Kayla and I were going to talk about our relationship, as well as our newly discovered sexuality as we both came out to each other as bisexual, and we were going to discuss our bisexual history. If things worked out, before it was all said and done, we'd be fucking like animals, making plans to cash in on our bisexuality in bed.
I can't wait to talk to her. I bring up my phone and notice a few texts. I'll get to those later. I bring her number up and call her. After one ring, she answers.
"Hey baby!" She sounds so happy and much better than last night.
"Hey beautiful! What are you up to?"
"Oh, just waiting for my turn to take a shower quickly before Katie and I start to pack up and check out. I can't wait to see you later on!"
The thought of Katie's naked fantastic ass covered in running water and soap suds is enough to give me a semi-hard cock. I actually find myself a little jealous that Kayla has seen it in person and up close on more than one occasion I'm sure...may have even done more than seen it up close. I shake my head and come back to earth.
" I can't wait to see you either, gorgeous. I think maybe we will be fuc---"
"Shit!!! I didn't charge my phone last night baby! Kayla cuts me off with. Well, at least we talked for a little bit.
"Well shit. Guess I'll talk to you later?" I say, a little defeated.
"Hold on one second!" I hear her in the background rummaging around in her bag. Moving her new sex toys out of the way, I'm sure. "Yes!!!" she yelled in the background, before picking up the phone again. "I brought my tablet with me just in case! Can we FaceTime?"
"Absolutely! I'd love to see your beautiful face anyway." I say, trying to layer on the charm. I really want this girl taking my dick tonight.
"Perfect! Give me a few seconds and I'll call..." and the call ends. Her battery must have died. I laugh to myself. Either she spent the night holding her phone and waiting for a text or call, or in the heat of things, she just forgot to charge her phone. Either was possible, and she certainly had a history of both.
