u/AdLarge1184

A couple of days ago I posted on my first time meeting a man after years of fantasising and leading guys on with chat. I posted that he wanted to meet again in a more relaxed place to explore more in discretion. He wanted to arrange a meet for the Wednesday after but was delayed through my shame and concern after my first time.

After days of constant messaging we arranged to finally meet up at his yesterday morning while his husband was at work.

The arrangement was simple, walk in strip down he would fuck me like last time (minus cumming inside me) cum on my cheeks and I go, I could manage that and had talked myself into just that.

On the drive over I recieved texts seeking updates on how far and pictures of him nude in his bed hard (not hung like a horse but just over 6 inches to a virgin, he may as well been). And while I was excited I was also incredibly nervous. Passing mums on there way back from the school run as I turned into his cul-de-sac the shame bubbled up again, my god what if they knew what I was up to, how could they I argued with myself but still as I parked just up from his drive way I sat for 10 minutes nervously watching each one pass waiting for a deserted road. Bing, where are my phone would ask, bing hurry boy I'm horny it would remind me, bing are you still coming it desperately asked. Yes I finally replied 1 minute away.

Remember lock the door behind you, I'm in the back room the only door open up stairs. Fuck here goes nothing.

I hurried down his drived, anyone in the uk yesterday will have know the weather was shocking. His door unlocked I slowly open closed it behind me and turned the lock, his stairs infornt. I took of my shoes, and pulled both my hoodie and tshirt in one and started to loosen my jeans as I climbed the stairs half naked finally dropping jeans and boxers at the top, naked but for my socks I approached the open door.

The small back room with a small guest bed and him naked cock in hand staring me down quickly came in to view. As he saw he the mid 50s man shuffled of the bed and stood as I entered his rough hand instantly groping my bare cheek. I was beginning to think you wasn't coming he whispered his fingers working down my crack (if your expecting romance turn away now) his other hand reaching for my semi erection as I reached down to my thigh to take his wet rock hard cock in mine. The room filled with only the sound of his horny breathing and my nervous huffs my hand working him slowly as my own cock decided to finally grow hard.

As his finger started to work its way in to me I tightened up my hand starting to stroke him off at pace his hand wondering from my cock up my body. My god your beautiful he whispered, I suppose thats what all older gay men say to younger naked lads in the bed room before sex. As his finger reached knuckle deep he leant over his rough stubble grating my chest as he started to lap and suck my nipple, fuck I stood like a statue this wasn't the plan I let out a nervous sigh and rested my hand on his head. The point again had come unexpectedly. Do I pull away, walk back, this wasn't the agreement or do I stay and hope he gets back on track, the answer came moments later as he lowered himself to his knees and inhaled my 7 inches (it was impressive until I thought hes had 35 years of practice) ive said before my wife gives head, but nothing like this the ease his mouth glided down my shaft, no gaging as he held himself balls deep and the suction applied as he worked back up was genuinely impressive and arousing. As I watched his bolding head work back and forth my fingers ran through his short hair I looked up and listened to that beautiful noise giving head makes and finally started to relax. Within about 3 minutes the building sensation of orgasm reared it head and I must have moaned as he pulled away saying something I didnt catch, sorry I begged say that again and he stood.. you cock tastes so good he smiled (having now tasted cock I don't think it does) he took himself in his hand placed his other round the back of my neck and gently ushered me to my knees which without any resistance I did. He shuffled forward slightly and without protest I meekly opened my mouth and placed my lips round his head. I'm no expert and sufficed to say the oral I proceeded to administer was slow and involved mainly licking and sucking head occasionally attempt to work my way down his shaft (it was my first try)

After what seemed ages of this he finally must have got bored and stepped away directing me to bend over the edge of the bed. Applying lube to himself and my hole I finally felt him against me, back on track after 10 minutes.

I'm not going to lie, it was painful as he forced himself in, i arched, I pulled away slightly, I moaned go slow but in seconds his hips where touching my cheeks, his hands firmly grasping my hips and the slow rock of anal sex started. His hand worked up and down my back as he softly gyrated against me, this was pleasant, this was good, this made me moaned and while still slightly painful moans of encouragement, and he picked up on as he started to extend the thrusts what started as a hip to ass gyration became a soft straight up thrust with the gentle sound of skin against skin, the rhythmic creak of the bed and my moaning.

Pleasant soft sex started to give way in minutes and I don't blame him he must have been stroking for the best part of 30 minute before I got there, his urge built quick and my god I felt it. The soft thrusts gave way to longer, hard, faster strokes as he hands pushed down on my back the bed creak gave way to an almost continuous sneak, I gripped the towel covering his sheets hard and buried my face in it as he achieved full fucking flow my god it stung, as I moaned into the mattress he grunted like a silver back claiming his prizes.

You want my cum he huffed I wanna cum in you boy he grunted I could only muster a weak grimaced yes daddy, I failed myself again and as the daddy grunted and growled in victory the warmth of his masculine seed filled my passage deliberate thrusts pumping his content inside my married cunt, my own cock welling in desperation started without any effort to count down, my whole body stiffened as I orgasm on his cock. My seed spilling out over the towel.

I'm a mid 30s married man that has for some time been using grindr to talk dirty and get myself off over my gay fantasies, but in 4 years I've always stopped short of meeting. I must admit I've led guys on and pissed afew off by arranging meets then chickening out last minute.

This friday changed all that after chatting with an older man for weeks (he's gay, mid 50s and married). We had swapped pics, went through the usual dirty chat, sent vids etc. We talked about meeting up what he would do to me and I thought the same as always, it wouldn't happen.

Last Wednesday we arranged a meet, he would take his lunch break, we would go to a woods down the road and he would take my cherry. This time I gave out my personal number which I haven't done I a long time and we exchanged texts. Friday came and exchanged some horny chat, as the time came closer I was out grabbing coffee a few miles from the woods, stringing him on I sent dick pics from the car as he constantly reminded me of our 'date'. While I started to drive home about 10 minutes before the meet time I got a call from him.

I freaked I've never directly spoken to anyone from grindr so I didnt answer. 2 missed calls later he rang again and feeling a bit pressured (guilty as he had left work) I answered.

He sounded so normal I made an excuse for not answering and apologised, he asked how far I was and as I approached the turning to take I found myself say 5 minutes. I panicked, he started telling how hard he was, how the layby to the woods was clear and asking he how far, I counted down the minutes and before I knew it I turned onto the road he was on. My heart was pounding as I pulled up slowly behind his car, he stood beside it looking like a normal guy. As I switched my engine off he approached, I felt like I couldn't just drive off now and got out to great him. He shook my hand and introduced himself with a smile and made some crap small talk about traffic before gesturing to the gate adding shall we go.

Fuck I thought as I watched him scale the gate and I followed down a small path into the trees, a place he knew well. Ive never touched a dick let alone had one inside me as I promised him. About 5 metres in he stop smiled and his hand grabbed my crotch, I wasn't hard was to nervous he must have know I was as he unbuttoned his jeans and pulled them down to reveal his rock hard 6 inches. He took my hand and placed it on his cock and asked if I was ok, I stupidly replied yes and started to stroke him as he rummaged round to pull my flaccid cock out, we stood for a few moments each others cocks in hand before he told me I was beautiful knelt down and took me in his mouth. I can't lie its been a while since my mrs has had her lips round my cock and it felt good and from a man that has far more practice than her it wasn't long before the nerves eased and I grew each time his head rocked forward and back. He pulled my joggers down to my knees as he gently sucked my to complete erect, and at just under 7 inch he took me effortlessly. But just as I started to enjoy him his mouth parted as his hand stroked me he looked up and asked me to turn round, he talked about rimming in our chats and was eager to follow through. I've never been rimmed and if im honest i didnt really get any pleasure from him licking and tonging my hole with his stubble scratching against my skin, but he seemed to be passionate stopping every few seconds to ever bend me over or pull my cheeks apart before again going at it.

After only a couple of minutes he got to his feet his hand on the small of my back pushing he over more and I felt his manhood on my cheek. Your gorgeous he repeated as I felt him pushing against my virgin hole and my god it hurt.

Holy fuck I'm getting fucked by a man and as he forces himself in me it hurts. I pulled away and whispered (i dont know why) for him to go slow. He then slipped a finger in me to stretch me before once again I felt his cock pushing against my ass. A few slips up and down before I felt his head penetrating my ring. I let out a fuck a shuffled forward only for him to follow pushing in deeper as I braced myself against a tree.

I wish I could say it was beautiful or romantic but I can't. Once he had forced himself (consensually) in me he immediately started thrusting long slowish strokes at first but with in a minute that gave way to fast short shoves. The pain had barely started to subside before he thrust deep his breath huffing.... for those on here that have felt it, feeling a man cum inside you is a strange sensation of warmth. Within seconds he had emptied himself in me. There is no romance in it, just a matter of fact business like process. As he stepped back he reached down to pull out some wet wipes....

I won't bore or disgust you with the details of cleaning up after, but although it was brief and painful as I hoped back over the gate I felt a rush. I didnt cum during the encounter, instead I drove home with his seed inside me and cum harder than I have in years. The last 3 days I have felt a shame, not just the cheating, but the pleasure and the panick of letting him cum in me. He has text me over the week end and has shown a recent STI check (both him and his husband play away) but i feel ashamed I even let it happen and how easily I gave into it.

He has a day off on Wednesday and is asking if I want to meet again, this time with no rush, in his bed both naked. Ive fantasied for years about something like this but should I go?