A Craigslist hook up with a surprising twist

I had had several encounters with men. Not a lot but enough to know I loved pleasing a man and his cock. I also loved an expert blowjob from a man. I had only tried one Craigslist hookup before and it was far from great. The guy was at least mildly mentally unstable and a creep. I wish that was one I could erase from my memory. I tried quietly and discretely to find a male lover to enjoy but always struck out.

There was bookstores many hours away and the climates there were extreme. Either extremely good or extremely creepy or totally a wasted effort. In desperation I searched Craigslist again. I found a very interesting ad. It said Are you looking to explore? Meet with me and let’s discover each other. Can host, live alone, safe and sane. That sounded way too good to be true. I remembered my last encounter and closed the tab and deleted my history as usual and went to bed.

All the next day and half the night I thought about the ad. I found it again, mustered my courage and sent a response. Bisexual married man, mid 40’s, cut, thick, clean and sane as well. Would like to meet and discuss possibilities!  I nervously hit send and waited on a response. I sent it at 7:00 pm and waited not so patiently for his response. 10 pm my email dinged. It was a semi nude pic of him in an open bathrobe and an invitation to come to his house and meet him. No pressure he said if your not comfortable we will part ways and no worries.   He sent me hi cell number and said text me if you want to meet.

I held my phone nervous for a long time before I entered his number and said. Hi this is Steve. I messaged you on Craigslist and yes I would like to meet. Are you free tonight?  He responded right away and said yes I am. Please come by!  He told me directions to an intersection I knew and said when will you leave?  I said I shower, throw on some sweats and head there in 10 minutes. He told me text when your there and I’ll direct you to my house.

I quickly and nervously showered, dressed and left to meet with him. I texted him when I got there and he said I see you. Next turn take a right and first driveway turn in and come to the door. He was watching me I guessed. I parked and walked up to his door and he opened it waiting for me. He invited me in and told me have a seat and offered me a drink. I gladly accepted. I was very into sex with men but with such a limited amount of gratifying experiences I was very nervous. He was dressed casually as well. Seemed very down to earth and sane. What a relief.

After I finished my drink he asked if I was willing to try. He had to sense my nervousness. I said yes. He was shorter than me, very soft spoken and I already felt more comfortable around him than i expected to. We stood up offered his hand and guided me to his spare room. He jokingly said this was the sex room. He undressed and I quickly followed suit. He moved closer and put his hand in my neck and pulled me down close to kiss me. I resisted a little and he said he really liked kissing but I didn’t have to do anything I didn’t feel comfortable with.

I liked that and instantly liked him even more. I leaned in and tried a small kiss. I did like it! At least with him I did. I leaned back in and he took over. Passionately kissing me and holding me close. His hands roamed my ass and mine his as well. I was loving it and getting hot fast. At last he broke the kiss and said what did I want to try first. His cock was hard and sticking straight out so I dropped to my knees and touched his cock. Fondling him and his balls. I inched further and put my lips around his swollen head.

This is what I wanted!! I love a cock in my mouth normally but now I wanted to suck this man into ecstasy. I sucked lightly savoring his taste and his lovely cock. He held my head lightly and whispered I see what you want!  I lowered my head and took all of his cock. Slowly tantalizing him all the way down. It wasn’t huge or excessively thick. It was perfect. A perfect fit for my mouth and hopefully my tight seldom fucked ass. I worked him over giving him the best I’d ever given. He then pulled me up. Enough, let’s save some for later! He was breathing hard now.

He told me to get on the bed and lie down. He crawled between my legs and licked and caressed my cock and balls. He teased me till I was trying to push my cock in every time his lips sucked my head. Finally after an eternity of teasing he sucked my cock inside his wet warm mouth and started to suck me so good I was moaning loudly and loving it. He sucked me for several minutes and got up and said my turn!  He made his way up and fed me his cock. He slowly face fucked me caressing my face and head while he fucked my lips and mouth. This is how it is meant to be I remember thinking. If only this could last all night.

After several lovely minutes of feeling that gorgeous head between my lips and across my tongue, he pulled out and asked me....be honest. What do you want to experience the most. Sucking me till I cum or can I fuck your sweet ass and empty myself inside you. Fuck me, please, I said. He smiled a huge smile and told me to roll over. He got some lube from the bathroom and returned lubing up that gorgeous cock. I was nervous but I wanted this bad. Really bad. And I wanted him to fuck me all the time!  WTF did I just think? Was I feeling more than I should from this casual no strings meeting?  

Hell yes I was. I felt feelings inside I’d never felt for another man before. As he approached I rolled up on my elbows and pulled him in for another kiss. I was losing it I thought!  He kissed me back and his tongue entered my mouth! I thought this was one of the most intimate encounters with man or woman I had ever had. He said fine. Have it your way!  He rolled me on my back, pulled my legs up and pinned them behind his arms. He bent close and said guide me in handsome, I need your ass!

I reached awkwardly down and guided his slick cock to my ass. I rubbed it a couple times to lube my ass and told him there when I was ready. He pushed inside firmly but not forcefully. I could tell he was holding back to not hurt me. His cock was deep inside me right to my limits of pleasure, a slight tinge of pain but nothing I couldn’t handle or wouldn’t handle for this man. He lowered his head and said, ok so far? Yes it feels good I said. A little tight but I’m ok. He leaned further in and covered my lips with his and started a slow rhythm riding my ass and passionately kissing me and licking my neck and earlobes. His heavy breathing in my ear was magic! I was hoping he might start talking dirty but his breathing would do just fine. He was getting really excited as was I.  While he stroked my ass with his cock deep inside me my own cock throbbed and stretched the skin it was so hard.  He increased the speed and leaned back so he could go deeper. He also held my ankles further back to get more access to my ass!

He started fucking me in earnest then. Never brutally just excited and passionately. After several minutes of his cock working in and out of my tight ass he asked me where could he cum? Inside me I said, please fuck me and cum inside. He slow stroked several more times then all the way up to his balls and he started cumming hard. I could feel every spurt inside me and every pulse of that beautiful cock. He stayed in for a minute and slowly withdrew. That was great he said. But you have needs too!

He eased down and gave me a great blowjob and I came in minutes! My thick cock filling his mouth hard and fast. He pulled up and left to clean up. He said I was free to use the bathroom, clean up and leave. I was stunned! All those feelings and emotions crashed around me like a ton of bricks! Clean up and leave? Ok I did. I drove home even more confused than when I started. How could I be so stupid I thought. This was just a hookup. How could I be feeling this way anyway? It didn’t make sense and wasn’t like me at all. I sat in the car for several minutes hoping I’d get a text with an apology or a goodnight, goodbye or something but it never came.

I went in showered and went to bed exhausted and confused. I saw his ad again after about 6 months. I so wanted to contact him again but decided once was enough. Fool me once I thought and went on with my life. It wasn’t a total wash I figure. I did discover I could have feelings for a guy that were beyond his cock so that’s a huge plus. Someday I would find the right one and have a regular encounter with someone I cared about and lusted for!    p.s.  I still stroke my cock on occasion remembering that fuck that night. And I still blow huge loads reminiscing!