My name is Dan, and I'm a relatively fit 45 years old, MWM. I stand six feet two and weigh around two hundred and ten pounds and am masculine and muscular. I workout regularly and have been told I have a hot body. My relatively tame m2m experiences didn't start until after I turned 40. But for many years before I sucked my first cock, I often fantasized about being with another guy. These thoughts would creep in while I had sex with my wife, especially when I sucked her cunt and tongued her clit. My mind would wonder what it would be like to have a cock in my mouth. While I fucked her, I would sometimes fantasize about being on the receiving end? About 10 years ago I started to surf the internet and get charged watching gay porn.
My fantasies started to get closer to reality once craigslist came along. After cruising the personals for several years I finally responding to several ads, and hooked up for a few quick JOs and BJs - all very awkward. My first cock that I sucked was a very small stubby from a very hairy guy that was understanding and surprised that I wanted to tongue his thick but short cock. Anyway, these fleeting encounters just weren't enough to satisfy my desire to go all the way. Over time I crafted a plan to act on my desires to spend the night with another guy with the intent to go all the way and be a submissive bottom.
The time came when I was on a business trip to San Diego. Upon arrival in the city I headed to my hotel on the water and tubed up craigslist looking for mature married dom top who was looking to play for an extended evening. The stars aligned when I read the posting from a MWM mid-fifties attending a convention in the city. His body picture showed an average middle aged guy with a hairy chest and medium sized cock. The thing that turned me on was that he spend two paragraphs describing his desires to mentally dominate another married male, while being a firm but gentle top man. He wanted someone to come to his room, obey his orders, and agree to not touch their own cock while he was being serviced. His ad assured that there would be no pain, only safe play, and that he respected his partners limitation. To be honest, I didn't even care too much about his age or that he had a modest gut. After reading the ad I immediately knew I wanted to used by this stranger as a sex object. I sent off a response with a body shot. He responded within minutes that he thought I looked great, and that he wanted to meet, have a drink, discuss my desires, and if the chemistry was right, we would head to his room for fun. We decided to meet the next evening at 9 p.m at his hotel bar. His email told me to clean myself (I had to ask him what that meant - he told me to go to the drug store to buy an enema), and be prepared to be a little sore the next day.
The next evening, I headed out in my rental car to his hotel, parked on the street, and went looking for a gentlemen of his description in the hotel bar. I spotted him very easily and he was indeed a distinguished gentleman, with nice salt and pepper hair, and good looking guy. He stood and gave me a firm handshake, introduced himself as "Bob" and ordered me a beer. I said, "nice to meet you, I'm Dan". After the beers arrived, I drank mine rather quickly as I was fairly nervous. He nursed his and spent what seemed like an eternity making probing conversation. He asked if I still slept with my wife - which I still do and enjoy - and wanted to know why a masculine guy like me wanted to know have a submissive experience. To be honest, I didn't have a good answer to that, other than I have always had strong m2m urges since childhood, and knew that sucking cock and mutual hand jobs just weren't enough. I also told him I had never bottomed and wanted to be instructed by an experienced partner on how to be a submissive partner. I added that my hook-ups only occurred about once every year.
Bob told me that he still loved his wife and had periodic sex, but that he had developed a relationship with a buddy back home (also married) in Alabama. Their wives were friends, and that he fucked his buddy regularly. In a very matter of fact way, he then told me that I was much better looking and in better shape than his friend back home. After paying the paid he said, "I'm going to have a lot of fun with you when we get upstairs". He then got up and started heading to the elevators. I followed like an obedient puppy dog. While we were taking a ride up with other hotel guests, I kept thinking to myself "what if they knew I was going up to a room to be fucked by a total stranger?" Believe it or not, that thought started to get me really turned on.
When the doors opened, we took what seemed like a really long walk down his hall way to his room. My heart was pounding the entire time and I kept thinking to myself - "Dan, are you really going to finally do this?" Reality fully set in when he opened the door, closed it, and ambushed me with a passionate kiss. That was my first m2m kiss, he must have noticed my surprise, and told me that my mouth would be touching more than his tongue in a few minutes. Bob then ordered me to undress and put on the hotel robe but to leave it open so he could see my body. I did as he told me. Once undressed, I walked into the main area of the room to see him still fully dresses sitting in an arm chair. Bob told me to stand in front of him. Again, I did as i was told. Bobs eyes never left my cock which was already standing at full attention, pre-cum forming on the tip. After about a minute of his admiring gaze, he told me get on your knee, undo his belt, open his jeans and see what will be occupying my mouth and ass for the evening.
When I popped open his pants, I could see he didn't have on underwear and his cock was already hard. At that point he reminded me to not touch my cock while I serviced him - specifically he ordered, "I want you to be begging to cum before I am finished with you." I said, "yes sir - and meant it!". I then pulled his jeans down just enough to release his full package. Bob asked if I was a good cock sucker - I said "I think so, He said he would be the judge. Bob then grabbed my head and aligned my mouth near the base of his 7 inch cock and said - "lick the shaft, but don't you dare take the whole cock in our mouth until I tell you". Obediently, did as was told. He remarked that I had the potential to be a great cock sucker. I touched his balls gently as instructed, and pretend that his cock was a lollipop. After a few minutes to told me I was now allowed to suck his entire cock. I couldn't wait to get that head in my mouth and taste the pre-cum that had formed during my shaft licking. That action received the highest praise so far... "yes, you are an awesome cock sucker".
I was on my knees for about ten minutes during which time he instructed me to go fast, then slow, then lick his balls. I obeyed every order and loved every minute of his firm instructions. I could see he was edging and getting more excited. When it was clear that he was close to blowing, he stopped and pull my head up, kiss me passionately with his tongue. After a quick tongue dance he said with a grin "Are ready for your next lesson?" He then stood up, removed his jeans, and took off his shirt. I initiated the kiss this time and told him "thank you for taking charge". He responded that he would tell me exactly how a submissive bottom should act.
Bob took my hand and walked me to the bed, and pulled the bed spread back. Without prompting, I got on all fours with my ass pointing toward the corner of the bed. He went to the night stand, got some lube and a condom, and squirted the lube in his hand. Soon there after I felt cold lube on the bud of my ass. The feeling of his fingers working my ass made my cock tingle and dance in anticipation. He knew I was a virgin and that it would take some time to prepare me.
He masterfully worked one finger then to and then three. It felt different to anything I have ever felt or experienced. Once the initial shock of having something enter my ass had subsided, I began to really enjoy the massaging feeling of having my ass opened and prostate probed. Once it was clear that I was getting
comfortable - my moans must have sent that signal loud, Bob repositioned me on my side in a fetal position. Bob told me that he wanted me to feel his cock impale me completely. I laughed and blushed at that comment, but told him I really felt like a horny virgin about to be taken. Never a truer word has been spoken about the experience I was about to have.
Bob pushed my legs up so that my knees were on my chest and positioned himself next to me to spoon. For the next several minutes he rubbed his cock up an down the crack of my ass, occasionally pushing his head into my eager bud. he kissed my neck and turned my head so our lips could touch fleetingly. At the end of this intense foreplay I was begging him to enter me. His positioned his cock head and finally push into me just enough so that I had the intense pain being violated for the first time. He heard my audible gasp, and stopped for just enough time for me to catch my breath before he resumed his thrust inside of me. Before I knew it, he cock was completely inside of me and I felt for the first time a complete feeling of fulfillment.
That is when real fun started. His cock started to piston my ass slowly and then quite fast. My moaning spurred him on. He kept up a rapid commentary with several colorfully phrases like "you really like that cock in your ass" to "that moaning is getting even harder and is only going to get louder" to "I'm going to fuck you like the bitch that you are".
He then got on his back and asked me to mount him. The best part for me was seeing his eyes and having him touch me while I slowly rode his cock. After I put his cock back into my ass, I moved down to kiss him and rhythmically move my ass onto and off his cock while tonguing his mouth. My cock was harder than ever before and dripping with pre-cum. Bob wasn't being as verbal as his mouth was occupied by my tongue but he was being more attentive as a lover feeling my chest, legs, and cock. We fucking like tigers for at least 10 minutes.
I then took charge by getting onto my back without asking. He didn't mind my only act of personal initiative during our entire encounter and instead moved on top of me with gusto. I knew he was ready to blow soon and wanted to finish me off. I instinctively put my spread my legs with my knees against my chest and which allowd Bob to re-entered me. Once his easily entered my ready ass, Bob started to fuck me like the slut I had become. My prostate was really being stimulated and my mind was so excited that I surprised myself when I started to cum like never before. Ropes of my cum spurted to my chest and my ass clinched with each wave of the orgasim. The action keyed Bob's own orgasm. I could felt his cock grow and throbs as it ejaculated into my ass. I pulled his mouth to mine as we both simultaneously orgasmed. We both bucked like teenagers.
After we both had cum, Bob colasped on top of me and I felt his cock slip from my used ass. He rolled off of me, and we kissed on our sides. It was the most intense sexual experience of my life and I told him so. He removed the condum and showed me the load that I had administered from his balls. If I had known him longer and was totally sure he was disease free, I would have loved to take that load in my ass and feel the cum dripping from between my cheeks. Anyway, I was glad for the experience and now know that I'm a total bottom.
Let me know if you like this story... or not. It is based on true experiences with little embellishments. Maybe I can find another "Bob" during my travels.
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