It started as a regular Sunday morning. Sunshine was breaking through the blinds and I was naked with a raging hard on. I took a moment to gather my thoughts, thinking back to the night before. My girl and I had met up with some friends and had some drinks. Well, I had some drinks while she was my DD. My memory was a bit shaking but I recalled some very aggressive, passionate sex. Our sex life usually falls into one category… underwhelming. She is conservative, reserved and not too experienced in all the greatness that two people can enjoy together. For example, rimming her is a no go zone, as is her sitting on my face. Two of my favourite things to do to a woman.
So back to my raging hard on. It was up for about half an hour and it was still persisting. I was starting to think that this was more than just morning wood and I was going to need to do something about it. I text my girl to see if she was awake, really more of seeing if she wanted to come by for some morning sex. Negative. She was on her way to church. Alright I thought, what other options do I have. So I broke out my iPad and started cruising craigslist. I cast a wide net, men, women, trannies… it didn’t matter. My throbbing 7in cock was driving this search.
Within about 2 minutes I came across an ad. “Mature Gay Couple Seeks Younger Third”. I opened it up. There was pictures of this very fit and hairy old guy wearing a purple thong and another relatively fit older guy in briefs. I don’t consider myself to be gay, or even bi sexual but I do enjoy the company of men from time to time when the mood strikes me right. And that mood was in full swing that morning.
I quickly sent them an email describing myself, included a few pictures. One of my throbbing cock and another with me wearing a nice pair of women’s panties. I got a reply within minutes with a phone number so we could text. Our texts flowed nicely and it just seemed very easy to go along with. Eventually Bruce added his partner Lance to make it a group chat. We shared some more pics and discussed experiences, mostly mine as they were trying to get an understanding of what I brought to the table (besides a young hard cock).
From our texts we established that Bruce was definitely the top. In fact, he said besides having his ass kissed, licked or rubbed it was off limits. Lance was a bottom. A very submissive bottom. I typically identify as a bottom. Mostly because the one time I did anal with a women I could hardly maintain a hard on, it just wasn’t enjoyable. The one time I topped a guy it was OK. I came… hard, but the situation was very fucked up. Imagine me dressed up as a young women. Complete outfit right down to stick on nails, lipstick, fake tits and a wig. And the other guy was dressed up as a women as well. He was an aggressive bottom and basically fucked my cock. But that is a WHOLE OTHER story I’ll write about later. They were primarily looking for another bottom but preferred someone versatile so that Lance and Bruce could enjoy him.
So I lied.. a bit. I liked what I was hearing and they obviously liked that they were hearing so they asked if I wanted to meet up for a drink. At this point it was about 10:15AM so we agreed to meet at a pub in downtown Hamilton for 11:30. This would allow me some time to get ready and to actually get into the City.
I arrived at the pub a few minutes early. It looked run down and gritty, the type of place that is full of regulars and new people are considered outsiders. I walked in, it was very dark inside. I looked around and saw less than a handful of other people in there. I saw a booth just beyond the bar so I went over and took a seat and sent the guys a text. A few minutes later two guys walked in. One was easily 6’5, 200 pounds and just looked ripped through his skin tight white v-neck shirt. The other, about 5’8 150 pounds, fit, but nowhere near the level of the bigger guy.
They joined me at the booth. Bruce (the big guy) took a seat next to me and Lance sat across from us. Once we had some drinks in hand the conversation really got going. They were so easy to talk to and immediately I felt incredibly comfortable. By my second beer I was opening the conversation up and inquiring about their sex life. At this point I felt Bruces hand start stroking my leg under the table. Instant boner. I excused myself to go to the bathroom. Mostly to give me time to relax and get a grip on my increasing levels of horny. As I stood at the sink Lance came through the door. We chatted as he went pee. When he was done he spun around, cock out. “Do you like what you see?” I said nothing, just smiled. He walked over, took my hand and placed it on his cock. It was so thick, not overly long but thick, maybe the thickest white cock I had ever seen. I got lost in the moment. I dropped to my knees and took him in my mouth. All of him. I pushed it a bit too far and gagged. He pulled it out and zipped himself up. He kissed me, no tongue. “If you’re choking on this you’re going to vomit when Bruce is done with you” he said with a giggle as we both walked back to the booth.
We enjoyed several more beers and great conversation. It was now about 2pm. I was definitely feeling the booze and was at the point where I needed to make a decision. Stop drinking so I can get myself home, or do I keep going and we’ll see where this experience goes. I decided to have one more but asked for my bill. This was my way of making sure I wasn’t getting completely wasted today. Bruce paid for all of the drinks (unexpected) and as we walked out he grabbed my arm and pulled me against his body. “We’ve all had a lot to drink. Why don’t you come back to our place for a bit so you can get some of this beer out of your system before you drive home”
Sure! I thought. Let’s do this. Their place was very close by. In fact, their house was directly across the street. As I walked into the house I saw a sign above the coat rack. “This is a clothing free zone. Place all articles in the bins below”
Cute sign I thought as I proceeded down the hall. Bruce stopped me and pointed at the sign. I laughed and mentioned that I thought that was just a joke sign. Bruce and Lance explained how their home is always clothing free as its very liberating and enjoyable to strut your stuff with nothing on. I wasn’t going to argue. When I am at home I am usually naked too. So I threw everything in the bin and joined them in the living room. In the middle of the room was a big bean bag chair. Lance motioned for me to sit in it. Within seconds he was spreading my legs and kissing my thighs while his slender hands made their way to my ass. He motioned for me to flip over. His hands began exploring and caressing my cheeks, lower back and legs. I was in heaven. He kissed my checks and spread them apart. I felt his tongue on my hole. I tensed up. I felt a second set of hands on my shoulders now. Bruce whispered in my ear “relax bud, he loves rimming and you have a great tight ass that he is going to love”. Bruce continued to firmly massage my upper body while Lance’s tongue made love to my anus. Long wet licks right up my ass crack, he circled my anus and gently probed it with his tongue, all while his hands rubbed my thighs and ass cheeks.
I never expected someone to ever give my ass this much attention and it was incredible. I was melting away as these two men took care of my body. Eventually Lance started using a finger on me. I was so relaxed that I didn’t even tense up (a big win for me!). Normally anal for me hurts like hell cause I am so tense but these guys were treating me like a king and making sure I was in my happy place.
Eventually Bruce suggested we all move upstairs to the bedroom. When we got upstairs Bruce grabbed me ear and pulled me to the bed. Forcing his cock to my lips. I did my best to take as much of him in as a could. He was so long, atleast 8.5/9”. I was laying on my back as Bruce was hovering over my face, slowly pushing his cock in and out of my mouth. I couldn’t lick it all I could do was try and relax my jaw while he slowly fucked my face. This went on for a minute or two until his pace picked up. He started going faster and faster. I started gagging as his cock was hitting the back of my throat. While this was going on Lance was still working my ass.
I pushed Bruce off. I had tears running down my face and was struggling to compose myself. My first face fuck was definitely intense. Bruce jumped off the bed and moved Lance out of the way. I could hear Lance squirting lube on Bruces cock. Bruce didn’t waste any time. He pressed his cock against my anus. I relaxed and felt him press it deeper. To my surprise there was no resistance. My hole was relaxed and ready to take this massive piece of meat. Bruce was gentle, took his time slowly working it in. As time went on he would pump faster and harder. I asked if he could flip me over because I preferred doggy. Bruce agreed. I assumed the position and Bruce went to town. He was pounding my ass harder than any guy, girl or tranny had ever. I was moaning like a girl, it felt so amazing. Then he spanked me. “Oh Daddy! This is amazing” I moaned. Bruce started going even harder. His hands were on my shoulders, pulling me into his cock as he thrust into me. I was dying. He was destroying my hole and it felt incredible.
Lance slowly positioned himself under me so we could 69. Bruce directed me to put all my weight on Lance. This jammed my cock down his throat but gave me good access to his cock while Bruce towered over me. As he thrust into me I could hear Lance gagging. It was oddly enjoyable and a big turn on. I moaned again “Oh Daddy, fuck me harder” Bruce spanked my ass again and picked up the pace on his thrusting. I felt like I was going to cum. I was doing everthing in my power to prevent it. Bruce was beginning to moan as well. I could tell he was close to finishing. I sensed Lance was about to cum. He slid out and at the same time Bruce pulled out. I felt Lances cock slide in. He was so much thicker than Bruce but it still felt great. He pumped maybe six times and I felt it. He erupted. He gripped my hips and pulled me close, pump after pump, shot and shot of hot cum into my hole. I was getting close to cumming now, like point of no return. Lance slide back under me and took my cock back in his mouth. Bruce reentered. He meant business. His thrusts were so hard I felt like I was going to impale Lance with my cock. “Cum with me Daddy” I screamed. Bruce grabbed on tight and pounded me hard and hard. I could feel his cock swelling. Then he stopped, pushed deeper and held it. He let out of the loudest moan as he unleashed what seemed like one massive long wave of cum inside of me. I couldn’t take it anymore and erupted down Lances throat. He was gagging, I could hear him trying to not choke on my load. We all collapsed onto the bed. Bruce instructed me to sit on Lance’s face until all of their cum had come back out. I obliged even though I felt like I had just run a marathon.
I stayed for a bit after. I really felt that this could become more the kind of friends with benefits situation that I could really enjoy, especially if these two Daddies were going to treat me like a King everytime.