First-off a short introduction, I’m bi and not out so am usually discrete and rather cautious. While I am happy with my personal arrangement it does mean that encounters with men are usually few and far between.
I’m in my late 30’s and overweight but strong and some might say handsome. Clean cut, 5ft10, hairy chest, uncut (usually shaved) and pack a good 7.5inches although I am not much of a shower.
My story begins when I was bored at work and went online to check out the various hookup sites I am signed up to. An older man I know popped up and over the years we have always checked each other’s profiles but not really done much further. I was particularly horny that day and decided to just message him. I used to work in a building that he managed, serviced offices and such. A guy I knew was gay and always thought was a great laugh and a handsome older man.
To my surprise I got a reply straight away, we went back and forth a few times, exchanged numbers and I acted like I didn’t know him until eventually we agreed to meet at his office after work for an ‘interview’ where I would show him my proficiency in dictation. Not wanting to massively surprise him or freak him out I gave him access to my private pics, which have my face and waited to hear whether he still wanted to catch up…and waited…
It was only about an hour but it felt like an age, he texted me and REALLY wanted to meet. 5.30 couldn’t come quick enough, I checked out dick pics and his profile for a couple of hours, god I was horny.
By the time our meet up was due I was almost frothing at the mouth for some cock and nervously made my way over to the office block he managed. I walked in and smiled as I saw him and greeted him warmly. “Hi Jeff”, a tall, beefy and looking smart in his suit. I was casual as normal, jeans and a jumper. We shook hands as the last of his staff left for the day and he said out loud “Andy, let me show you the office I recommended for you on the phone. Oh, good night Anna see you tomorrow.”
I nervously smile as we got in the lift, we made awkward small talk as we went up. He guided me to an office door. I walk through and put my satchel down as he locked the door. I turned as he came over.
My cock hard in my jeans as I moved forward and on my toes to kiss him, I’m not usually a kisser but just go with the flow as the situation dictates. He was forceful and stuck his tongue down my throat holding me as he did.
With women I tend to be rather dominant, but with men and particularly with older men I seem to want to be dominated and submissive. I say this as Jeff broke off kissing me and pulled off my jumper squeezing and biting my nipples as he worked his way down to undoing my jeans. I kicked off my shoes and got naked, except for my socks. He smiled at my rock-hard cock and jerked it while kissing me until I asked him to stop for fear of cumming.
I then unbuttoned his shirt as I grabbed at his bulge wondering if it was bigger or smaller than the pictures in his profile. Licking and nibbling my way down as I got to his pants, unbuckling his belt and then unbuttoning his trousers letting them drop to the floor as I did. Looking up I smiled as I gently bit his bulge before freeing his cock.
Not my size but slightly thicker and at least an inch smaller. I cupped his now free hair balls as I licked the tip of his cock. Jeff released a soft groan and nudged me away as he got naked too.
We moved from the main office to a side room where we embraced and kissed as our cocks, leaking precum poked and prodded at each other. I quickly dropped to my knees again, taking him whole in one swift motion burying my nose in his hairy groin until I gagged.
I spluttered out his cock and panted as I laughed jerking him, I looked up and smiled. “You have a nice cock Jeff.” Before attacking it again, gripping his thick thighs as I bobbed on his cock.
Much to my dismay he pulled me up and kissed me, reaching for my cock again as we did, I tried to push him away but he held me tight jerking me. I relented and kissed him hard, whispering how I wanted his cock so bad.
He laughed and got on his knees, taking me in his mouth. Jeff lovingly licked and kissed my cock pulling back my foreskin and taking me in inch by inch, I groaned in pleasure as my legs shook. “Stop” I whispered, “You’re going to make me explode!” He relented as he stood.
We kissed again, I think because he didn’t want me blowing so soon and also he was pretty flustered as when I grabbed his cock he flinched as a string of pre-cum dribbled out.
Somehow, I ended up with my back to Jeff as he kissed my neck, and jerked me off, I was moaning as I leant forward. His cock slid between my arse cheeks, pre-cum glazing my skin, he began to poke his cock at my butt. I felt his head poke at my rim a pushed back a little.
I wanted him in me so badly, but I have never been a bottom and would prefer my first time to be with a condom, I don’t know maybe I should have just let him ram it home. I turned around to kiss him again, but he pushed me back and fell to his knees.
Jeff looked up at me as he licked the tip of my cock as I groaned, he sucked me length to tip a few times slurping loudly as I began to pump my hips, “I… I’m going to cum”, I moan pushing his head away. He clamped down and deep throated me as I sighed feeling my cock pulse and grow as me moved back holding only my head in his mouth. I erupted in his mouth, my legs shaking as I panted “Fuuucccckkkk”.
He kept sucking and swallowing, not releasing my cock until he milked every drop from me. Jeff released my softening member as he stood, I kissed him as we shared the last couple of drops remaining in his mouth.
As happens often when I cum with a guy, I lost my urge to do anything else and just wanted to get out of there. I got nervous and self-conscious apologizing. I felt bad that I didn’t reciprocate, but he was totally cool.
I think I owe him a blowjob to completion at the very least. Hopefully I can build on this story…