A Memorable Wor Trip

I was never that keen on travelling for work and dealing with the logistics of getting from place to place. Trying to find alternative transport or hotels when things didn't go to plan could be painful at times, which made me frequently consider changing to a job where I was based in one place. My perspective on travelling changed though after a trip which didn't go to plan but ended up being the most memorable trip yet. I was in my early 40s at the time and decently fit but not muscly in any way, I am naturally slim at just shy of 6 feet.

Landing at the airport I knew I was up for a bad night as the landing was delayed for an hour while we flew around the airport several times. This was all due to severe weather and as expected when I departed the plane, I found my connection had been cancelled. The airport was mayhem, thousands of people were stuck trying to find alternative transport or temporary accommodation. I was no different as I desperately tried to find a hotel for the night with no luck. As I continued to call around hotels I heard a man near to me securing accommodation somewhere, as soon as he was off the phone I asked him where he was able to book. He told me that it was the last room they had due to a last-minute cancellation but generously offered for me to share the room with him if I paid half. There was no consideration required as it was already very late and with little chance of me finding a better offer, I quickly accepted, and we headed off to the taxi stand together. He was a businessman probably in his early 50s, a bit over 6 foot and had an average build but he seemed normal enough to share a room with for the night.

Arriving at the hotel we took turns in the bathroom to shower and change before heading straight to bed as it was now very late. It was only a queen size bed but big enough for two men to sleep in and just still have our own space. I had showered first so climbed into bed without waiting and was out before he had even finished his shower.

A couple of hours later I awoke forgetting where I was, after a moment I noticed my right foot was pressed up against something. While laying on my side in my sleep, I must have bent my top leg back and my foot was up against something soft and scratchy. While manoeuvring my foot to feel what it was, I suddenly remembered where I was and that I was not alone as I quickly pulled my foot back down. My heart started racing with the realisation I had just fondled his groin with my foot and had no idea how long it had been there before I woke. Fear then shot through me as I pretended to be asleep praying that I had not woken him up with my unintentional exploits.

All was still for a moment until I heard him start shifting in bed and then his hand landed on my waist, followed soon by his shifting body which pressed gently up against mine. We were now in the spooning position and all I could do was stay in place and continue pretending to be asleep and ignore it. It dawned on me around this time that he must have come to bed completely naked, why would he do that if sleeping with a stranger? I would usually sleep naked myself but had put on a shirt and briefs that night out of curtesy. It was also apparent now that my foot had made him excited as I could feel his long hard rod up against my cheeks.

We lay there for a few minutes as he adjusted slightly here and there with his arm now curled around me and hand on my belly covered shirt. It may have all been involuntary by him sparked by my misplaced foot, so I lay there hoping he would eventually roll back on to his side. This did not happen though, as he started slowly rubbing his member against my backside. This was soon followed by his hand moving from my belly down to my groin, cupping it through my underwear gently. It was now clear that he was not asleep, his hand began massaging my groin while his cock slid up and down against my ass in a steady rhythm. I was not gay, but my penis said otherwise as it hardened up, clearly loving the attention of his hand.

Now that we were both erect, he slid down further, I felt him slip his cock in the leg of my brief then slide it up across my bare ass cheek. I didn't resist, so he continued to grind gently while his hand ran up and down my shaft. His hand soon moved above my briefs and came back down under the band of my underwear, touching my erect penis skin to skin. Electricity shot through as he popped me out of the underwear and was stroking me delicately. I must have been hornier than I realised as I should not have been letting him do this to me, I was happily straight. Pulling away from me slightly, he let go of my throbbing penis and with both hands grasped my underwear.

Quickly he pulled my briefs down over my ass and legs, his foot then snagged them at my knees and pried them all the way off. I was now naked from the waist down, hard as hell, and confused why I wanted him to snuggle back up to my half naked body and resume working my member. He didn't disappoint as he shifted back up against me firmer this time, with his cock nestled comfortably against the full length of my crack, with his hand returned to my aching penis. There was nothing delicate about his stroking now as he began beating me off, his other hand manoeuvred its way across to caress my balls. It was an amazing feeling being serviced in this way by another man, but it didn't take long for him to take me to the limit as my body started to spasm. As my balls contracted, his second hand moved up to my cock head as I started spewing streams of cum right into his hand. He kept milking me until my body relaxed, and then broke the silence by simply saying, "Good girl Cumming for Daddy".

His hands then returned to his side and I felt him wipe my cum against my ass, then he spread my cheeks slightly and smeared it against the hole. This made me tense up as I realised what his end game was. His other hand gripped my hip holding me still as his finger was twisting its way inside my body, using my own cum as lubricant. He shushed me quietly like you would with a baby and told me to relax while Daddy loosens me up. I didn't know what to do, the hand job was amazing, but I didn't want this but felt obligated somehow. He was now working a second finger inside me stretching my virgin hole further.

He returned to my now semi-erect cock to milk any post-cum as I felt him rubbing it over his cock. Removing both his fingers from inside me was a short lived relieve, I was terrified as I then felt his sizable cock head pressed against my ass hole. He started entering, as he broke through, he said "Relax baby, I'm going to make you a woman tonight". It was painful as he gradually slid further inside me, backing up at times before pushing further in, letting my semen do its work for him. Finally, he was all the way inside me. Asking if I was ready, and without waiting for a response, he started to slowly fuck me. He pulled my top leg up against my chest giving him better access as he pumped me.

I had always assumed anal would be painful and was not wrong, but as he continued expanding my ass and retracting, the pain subsided to a point that I could somewhat see the pleasure in being sodomised. I think he sensed this as he then rolled me onto my stomach and mounted me, never letting his cock slip out. He pushed my ass up a bit, this pushed my head into the pillow more. He was now fucking me a bit faster while leaning over top of me, he kept this up for a while before kneeling up and lifting my ass with him.

Picking up pace he was going hard, pumping in and out of me, even exiting completely before driving straight back in with force. This was again more painful but strangely pleasurable too, I was letting this stranger screw me like a call girl with no regard for me. He was clearly fit, continuing to slam into me for a good 10 minutes. Thrusting harder than before, he climaxed deep inside me filling my hole with his sperm. He was grunting very loud by the end so surely would have woken those in the adjoining rooms. For a minute he stayed slumped over me hugging my belly tight, deep inside of me, releasing everything he had. Eventually sliding his spent cock out of my anus, he fell off my back rolling onto his side of the bed.

He returned to spooning me as he pulled the sheet back over us. Kissing my neck gently, he thanked me for being Daddy's little girl for the night. I was in pain and worried he had done damage, but I figured that gay men do this every night so the pain must pass.

As I awoke the following morning, he was already dressed and organising transport to wherever he was going. I slid out of bed covering my shrivelled penis while I tip toed past him. As I passed by, he slapped me on the ass and gave me a wink while still talking on the phone, I felt like such a whore but secretly loved it. While in the shower, my ass was burning in pain as I washed the best that I could. By the time I finished showering and dressing he was gone. I found a thank you note left on the bench with a couple of hundred-dollar notes. He really wanted to treat me like his prostitute for the night, and although it made me feel cheap, I had never felt sexier. Work trips took on another meaning after this, I regularly posted on apps looking to pimp myself out to some random stranger for the night and re-live the experience.