The hottest night of my life

I'm Steve.  I am 35 years old and married my gf of 2 years a couple of years ago. I haven't been with a man since I've been married but I still think of my past experiences quite often.  One man is on my mind more then others.  His name is Rick and we had a secret 5 year sexual relationship.   Rick and I had a slew of very hot and kinky encounters but I constantly think of one night in particular, the first time we ever met.

I was 26 years old and enjoying my single life.  I was handsome, 5'10, was 160 pounds at the time and had short dark hair, brown eyes, tanned complexion, runners type of build.  I had my own place, a good job out of college, and stayed in shape.  I went on dates with some women after college but what nobody knew about me was that I was secretly into men as well.   I was watching gay porn constantly and my curiosity peaked.  I began having hookups with a few random guys from Craigslist.  Mostly just JO sessions and on a few occasions some really hot oral sessions. 

About two weeks prior to my encounter, I purchased a thick 8 inch dildo online along with copious amounts of lube.  Being as curious as I was about receiving anal, I began using this dildo on almost a nightly basis.   The more I used it, the more I wanted to try the real thing.  There was still a fear for me to take that next step but in moments of lust, it was all I could think about.  

It was a Friday night. I had been out for happy hour with co-workers.  I was expecting to have a drink or two and call it a night but my drink or two turned into ten.  My group started to thin out so decided to head back to my apartment.  I heading over to the subway. Luckily my stop was only 3 stations away so bot too far away. On my subway ride, I noticed a really hot, older, biker type guy.  Tall, bald, salt and pepper goatee, he was my ideal type of guy.  He'll never have any idea since he was with a woman at the time but I was checking him out the entire subway ride and that got me really horny. My stop arrived and I departed the train and Walked to my place across the street from the station. When I got back to my 500 sq ft studio apartment, I immediately disrobed and turned on gay porn in my laptop.  I went to a favorite video of a biker type dad fucking a hot younger guy and I was extremely hard.  What is now becoming a habit, I reached under my couch/foldout bed and grabbed my new toy.  The dildo was flesh-colored and had succion cup at the bottom. I stuck it to the wood floor and applied lube to the toy and my eager ass. I slowly lowered myself onto this thick toy and it felt so good.  I placed the laptop on the couch so I could watch the video while I sat on my new favorite toy.

As I began to slowly ride this thick 8 inch dildo, I decided I wanted more.   I decided to go to a online gay chat site.  I would go to this site now and then when I got really turned on. I would meet guyson this site and woukd usually engage in chatting about sex, cyber sex, roleplay, or sometimes phone sex.  I had never actually hooked up with anybody through this site before.  I logged in and immediately received a bunch of private message requests.  One of them stood out.  His screen name was divorceddad45.   His description sounded very similar to the guy on the train that I saw earlier so that grabbed my attention.  After exchanging pleasantries, we began chatting about ourselves and what we like sexually.  He told me his name is Rick, he is 45 years old 5'11 190, bald with goatee and is a total top.   We seemed to be the perfect match sexually.  He was a total top into young guys and I was looking to bottom for the first time and was attracted to men with Rick's profile. 

He then goes on to ask me where I'm located because he was curious and interested in phone sex.  I told him I was interested in phone sex and told him where I'm from and he replied back, "so am I!!!!". As soon as I saw that, a huge wave of desire came over me.  I had the feeling that conversation might possibly lead to actual sex.  I asked him what part of the city he was from and he was only about a 20min subway ride away.  

Rick asked if he could call me and I typed my phone number as quickly as possible.  He had a deep sexy voice and was really confident.  We chatted for a bit and then he asked me if I could email a picture of me and he'd send one back.  I only had g-rated picture available so sent him a recent picture of me at the beach a few months prior.  I cropped out the other people in the pic and was just me in swim trunks laying on a towel. He sent me a picture back of him in just his white briefs and an obvious rock hard cock sticking out of his briefs.  I loved his picture and told him so on the phone.   That prompted him to ask me if I wanted to meet.  I admitted to Rick that I was very horny but also kind of nervous since I had never received anal sex before.  He almost begged me to come over at this point.  After a short pause, I blurted out my exact address.  Rick told me how thankful he was and that he'd be over as soon as possible.

I became immediately excited.  My buzz was subsiding but I was still in extreme lust.   I laid out the couch to a bed and got on my back and started fucking myself with the dildo.  I stayed on my back and fucked myself over and over again until I heard the front door buzzer.  A wave of excitement came over me.  I took out my toy and put on my black briefs on and buzzed him to my apartment.   I then went over to the door and looked out the keyhole and as the elevator open, Rick walked out.  He looked really hot in his white tight tee shirt and jeans.   He knocked on the door and I opened.  We greeted each other and hugged as and let him in.

As soon as I shut the door, he pinned me against the wall and kissed me.  We kissed very aggressivly, pinning me against the wall and pressing his lips against mine.  He slides off my black briefs and takes off his tee shirt.  Feeling his muscular chest against mine got me on another level of horny. Rick had physical control of me and I really really liked it.  After a passionate stand up make-out session, he told me to go to the bed and "get on your back boi".  Rick took off his jeans and white briefs simultanously and his very hard 7 inch cut cock appeared.  He walked over to where my head was on the bed. I turned my head to the side as his hard cock apporached me and I couldn't wait.  The second his cock came near me, I reached out my head and went for it.  He grabbed a hold of my head and slowly worked his cock in and out of my mouth while he slowly stroked me.  

While he slowly fucks my face, he tells me how I'm lucky a daddy like him came into my life and how good of a son I am.  Rick is very verbal and he showed it right away.  Telling me how excited he is to take my "man virginity".  After a good 15 minutes of Rick fucking my face he pulled out of my mouth and climbed onto my pull out bed and got on top of me.  Rick and I started making out again and with almost as much passion if not more then when we kissed when he walked in.   We kissed and rolled around my bed for a while and then he moved his lips down my chest and down to my fully erect 6 inch cock.  My cock jumps as Rick's lips hit my shaft.  He also thusts his right middle and pointer fingers inside of me.  I was still lubed from my previous toy play so could here the swish of his fingers thrusting in and out of me while his lips move faster up and down my throbbing cock.

After about 10 minutes of this, we could both hardly take it.  Rick asked me if I'm ready and I smiled and nodded.  He climbed back on top of me and places both of my legs over his shoulders.  I looked up at him as he hover over me and I was completly in lust with him.  At that moment he was the sexiest man alive and I wanted him.   He lowered himself on me and kissed me while his cock head touched my virgin pucker.  I had been looser due to my prior toy play but it still hurt as he slowly began to enter me.  I was so turned on feeling a real cock slide into me for the first time. Despite my constant 2 week toy play, feeling a real cock was a revelation.  It hurt at first but I lived it.   Rick took it slow with me for the first 10 minutes as I got used to his very hard cock.   As he fucked me, we continued to make out like a horny high school couple. He'd tell me how cute I am and would ask me how I liked daddy's cock.  Of course, my response was "I love it" with a wide grin.

This prompted him to really start fucking me.  The pain subsided after a while and Rick fucked me faster and faster while I lay defenselessly beneath him as my legs dangling over his shoulders. All I could hear is my pull out bed/couch slaming against the wall while he told me how much he loved fucking his boi and I'm lucky be fucked by a dad like him.   The longer he fucked me, the more in love I became with his cock (and him as well).  He then told me to bend over and place my face on my pillow and he began to bang me from behind.  Thrusting and spanking me, feeling the pain from doing this new position to me and his heavy spanks.  He then says, "I love your face boi, get back on your back, I want to see you when I cum".  I get back on my back and he placed my legs on his shoulders again and he starts fucking me and kissing me.  My back arched, my legs pointed to the air, both of us moaning, it was like the hottest porn I had ever seen but I was actually living it.

Kissing me while Rick thrust his cock in and out of my ass, he asks me where he can come.  Now not my safest or most sound decision safety wise, but I really really liked him so I said "anywhere you like, daddy". He let out a "oh yeah!!, what great boo you are" and fucked me harder and harder for 5 minutes and then i could feel him swell in me. Rick yells, you want my cum boi, tell daddy you want my cum".  I told to "cum in me daddy, cum in my virgin ass".  After a few big, hard thrusts, he slams hard into me one last time as he begins to grunt and groan as he begins to cum and lets out a very loud oh yeah while I feel him cum in my ass. Rick kept his cock still, deep inside of me so I could get every last drop of his cum.    I was so turned on.  My cock is still rock hard as he slowly pull out of me and I feel his cum leak out.  He then stood up to wipe his cock off with a towel near the bed while he tells me to stroke my cock.  Rick set at the foot of the bed and told me to cum for daddy.  I looked at him and moaned oh daddy as i began to get close and finally shot the biggest load of my life.  My chest covered in cum, my shot so long that I even got some in my mouth and on my face but most of the cum laid directly on my smooth chest.

He came back to me and laid on the bed next to me and we kissed.  After making out for a while again, Rick told me how hot I am and he wanted to see me again.  I was so happy, I told Rick that I'd really like that.  This began an extremely hot 5 year relationship.  I am looking for to sharing more about our hot sessions :)