| Ah, the life of a Salesman. When not on an airplane or in a car, I can most likely be found in a manufacturing plant pushing my wares or passing the time in a hotel room. This glamorous career of mine his driven away three wives, thankfully no children have been involved. After my third divorce I promised myself not to get married again until I stopped traveling or retired.
About a month ago I spent some time in the Chicago area. I had been there more times than I care to remember. After the first few visits I found a nice, centrally located hotel, not having to pack up and change hotels during a visit is always a treat.
I landed in O’Hare just after 11:00pm, finally walked into my hotel room at nearly 1:00am. After hanging up my suits, unpacking my bag, filling in the room service breakfast card, and setting a wake-up call, I groggily undressed and pulled on my short white nightgown and was asleep before my head hit the pillow.
It was my third wife who introduced me to women’s sleepwear. On my first night back after a particularly long trip overseas, my wife pampered me through the evening. The jetlag was wearing on me, and I know she noticed. So early in the evening, she drew a hot bath for me and set candles around the rim of the tub. I soaked for a short time and decided to get out before I fell asleep and drowned.
After drying off I went to find my pajamas. My wife had unpacked my suitcase, of course my p.j.’s were in the middle of the wash cycle. She happened into the room just then and realized what had happened and knowing that is the only pair I own, she pulled one of her clean nightgowns from a drawer and apologized unnecessarily.
Being too tired to care, I pulled it on and fell onto the bed. A ‘tent’ soon appeared under the gown which had required no external coaxing. The smooth feeling of the silky material did something to me. My cock became harder then it had been in a long time. Needless to say I found the energy to make love to her which turned out to be the best sex in our marriage. I have slept in nothing except nightgowns since that night and have accumulated a nice collection of different colors and materials.
Startled from my sleep by a knock on the door, breakfast already? Glancing to the digital clock on the night table, it read 5:30am. Not surprised my wake-up call didn’t occur, I scrambled out of bed and shouted through the door, “Room Service?”
“Breakfast is served.” A feminine voice replied.
“Just leave it there, thanks.”
Tip-toeing to the door, I waited until the sound of the foot-steps had faded and the hallway was silent. Then cracked the door open, no one in sight, I opened the door a bit more, bent down and grabbed my breakfast of oatmeal, orange juice and coffee. I heard a giggle from the far end of the hall by the elevators. Slowly turning my head I saw a young lady of Latin descent in her early twenties, dressed in the standard room service uniform, covering her mouth and giggling at the sight she was seeing. She hand long dark hair pulled up in a bun on top of her head. She couldn’t have been more than an inch over five feet, and I would be surprised if her weight was in triple digits.
I would probably laugh if I were in her position, a guy in his mid-forties, of medium height and weight, just having gotten out of bed, wearing only a dark green nightie with spaghetti straps that ended at mid-thigh, bending over in the hall picking up his breakfast. Yes, I would be laughing my ass off if I stood where she was standing, but I wasn’t.
I did the only thing that I could do, I picked up the tray, smiled at her and shouted thank you down the hall, quickly ducked back into my room before she could offer a reply. Having missed my wake-up call, I didn’t have time to dwell on what had happened, rushing around the room getting ready for the day ahead. Just before leaving the room, I reviewed my schedule, grabbed my briefcase and car keys and walked out the door.
The day was uneventful and passed by quickly, I avoided making dinner plans, looking forward to room service and the book I was in the middle of. The lack of sleep was catching up with me and I needed to call this an early night.
I arrived back in my room and called room service, as I pressed the button on the phone I remembered my encounter earlier that same day. Quickly shoving the memory from my mind I ordered dinner as I scanned the channels for the news. The man who took my order said it would be up in 30 minutes. And having stayed here before I knew 30 minutes meant 30 minutes.
Giving up on the news, I took off my suit and hung it up in the closet, changing into my denim shorts and t-shirt which was much more appropriate attire for Chicago in July. My dinner arrived right on time, I welcomed the young man into my room as I went to find a tip. He set the tray down on a small table and stood near the bed waiting for me. I turned to face him with a five dollar bill in hand, to find him flipping the pillow over on my bed. Under the pillow was my nightgown, it looked as if it were washed and pressed.
“Whatâ€¦” was all I could manage to say.
“Leslie, the girl who brought you your breakfast couldn’t help but tell a few people about the “man” in 515. The cleaning crew found your nightie on the floor and decided to clean it up for you.” this was said in a very commanding and condescending tone. “You should be more careful about where you leave your things.”
“What do you want?” getting scared at this point, this guy stood 4 inches taller and out weighed me by at least 40 pounds and all of it appeared to be muscle. His light brown hair was cut short and his bright blue eyes looked tense.
“Well, I have been wondering what you would look like it this thing.” He said as he looked at the gown hanging from his fingertip, “Put it on.” And he tossed it to me.
“You have got to be kidding! No way am I going to let you see me in this! What are you a fag?” I shouted at him taking a step toward him, all the while hoping to intimidate him.
My bravery was soon shattered when his open palm came out of no where and struck my cheek. I feel to the floor and felt the entire side of my face become very warm.
In a very firm voice he demanded, “Put the fucking thing on or do you want to get slapped around some more?”
Grabbing the gown and standing up while cupping my cheek, quickly considering my options, there weren’t many: #1-make a break for the door, he would surely catch me, #2-put up a fight, he would surely beat me to a pulp, #3-put the gown on and see what happens. It seemed to be the least appealing to my ego, but I said “Okay, I’ll put it on, just chill out. There is no need to get violent.”
He stood there with his arms crossed on his chest and nodded his head. Then starting toward the bathroom, he led the way and stood in front of the door to the hall. I closed and locked the door, scanning the room for a phone, nothing! Dammit! Why didn’t I spend the extra twenty bucks for a room at the Hilton across the street?
I heard the lock click and the door opened a crack, “Locking the door won’t stop this. Remember I work here.” He taunted me with these words.
I slowly disrobed, leaving my underpants on, and pulled on the nightgown. “Okay, it’s on.” I said fearful of what was to come.
“Naked under it?” he asked
Reaching down and sliding off my underpants “Yes”.
“Then get out here.”
I opened the door, where had he gone? Stepping into the small area between the door to the hall and the room, I momentarily considered running out into the hall screaming for help. Looking into the mirror, that idea quickly faded away. I walked into the room to find him sitting on the chair by the desk.
“Nice. Turn around let me see you.” He said while standing up and raising his hand, drawing circles with his index finger.
I turned around slowly, when I faced directly away from him, I heard a zipper. A chill shot up my spine. What was this guy going to do to me? Continuing my turn, sheepishly raising my face to see him kicking off his shoes, his pants unbuttoned and zipped, a large bulge pushing the limits of his white cotton underpants. “What? Were you expecting to tease me like a slut and then have me leave like this?” he said in a firm tone while grabbing his bulge.
Now I had never had a homosexual feeling in my life up to that point. But something about the position I found myself in made me reconsider my stance on all things sexual. My night gown was showing the tell-tale signs of my own arousal. All of the sudden, the foreign thought of a cock in my mouth didn’t sound too bad. And besides, what choice did I have? What the hell was I thinking? This guy was going to rape me!
“I guess not.” lowering my head, trying to sort out my feelings.
“Well I think you better get over here and take care of this before I bitch slap you again.” He commanded while dropping his pants and underwear, kicking them to a corner in the room.
Making my decision, I would do whatever the hell this guy wanted. Who would ever know anyway? I was a thousand miles from home, this would be just like any of the many flings I had had with various women over the years, only with a man. God, what have I gotten myself into I thought to myself.
Taking my first step on my way to him, what would this make me? A bi-sexual? Another step, just get it over with and he’ll leave, I can change hotels in the morning and no one will ever know. Finally the last step, I was standing right in front of him.
He placed his hands on my shoulders and pushed downward, I knew where this was going. On my knees in front of him, his cock almost touching my nose. Outside of the gym, this was the first cock I had ever seen. It was several inches longer than mine, but the girth was pretty close to my own. His balls hung low in their hairy sack and swayed and he shifted his weight, getting impatient I’m sure.
Almost gently he placed his hands on the back of my head and nudged me closer. The head of his semi-hard cock bumped my lips. “Do itâ€¦ now. And one more thing, if you bite, I’ll kill you.”
The words were echoing in my mind as I opened my mouth and took the head between my lips. It tasted of sweat and skin. Licking the underside, I felt it grow a little on my tongue.
This isn’t so bad, in my mind I put it in the perspective of eating an external pussy. It worked, I found the more enthusiastic I was the more he got into it. The sooner he came, the sooner this would all be over with.
Using some of the tricks my second wife used on me, she was a great cock sucker. I started bobbing up and down on his cock, coating it with my saliva, keeping pressure on the underside with my tongue, making it slippery. Increasing the speed at which I traveled along his tool, until I felt him push back into my mouth. His hands were still behind my head, they were just following my movements.
I guess I got a little too into it at this point, I tried to take too much into my mouth and wound up gagging, having to pull off completely to catch my breath.
“That’s enough of that.” He said as he grabbed a handful of my hair, and in one swift movement, pulled me to my feet and pushed me onto the bed. Quickly grabbing my hair once again and pulling my head off the foot of the bed.
Panic came over me, I tried to sit up to run away. He pushed me down and held me in place with a hand on my chest.
Squatting down, he lowered his ball sack onto my nose. “Lick ‘em boy. And remember what I said about your teeth.” As the word “teeth” was said, his free hand grabbed my erection. With his thumb and forefinger, he pinched the head of my cock. Just as the pain hit my mind, he pulled his thumb away but kept a firm grip on my cock.
I raised my head, his sack spread across the arch of my nose and my eyes were within millimeters of his ass. I stuck out my tongue and licked his ball sack from cock to bottom. The taste of sweat was much stronger here. There was something else to it, he tasted like what I imagined a man to taste like. I repeated this over and over until he tired of this too.
He slid himself forward until his ass was on my mouth. I struggled again at this point, no way was I going to lick somebody’s ass! He dropped his weight onto my chin and pinched my cock head again, harder this time.
My back arched, trying to get away from his grasp. I screamed, but his ass was nearly suffocating me, not a sound made it out.
He released his thumb and lifted himself up. “Lick it, NOW!” lightly pinching my cock head again, a warning of what was to come if I didn’t comply.
My entire body was covered in a thin layer of perspiration. The head of my cock was throbbing trying to recover from the abuse he had inflicted upon it. And in my gut, I felt the beginning of what I was sure was going to be a very powerful orgasm.
Sticking out my tongue, the very tip of it made contact with his hairy asshole. I bumped his tight muscle with my tongue, not sure what the hell he expected me to do.
“I said LICK it, not play with it.” Quickly pinching once again.
Flinching from the pain then sticking out my tongue as far as it would go, lapping at the crevice between his butt cheeks. I felt like a dog at a bowl full of water. The taste and smell of shit assaulting my senses. Not stopping for a second, feeling his hand wrapped around my cock.
His other hand had eased up on my chest and was lightly pinching my nipples. Once they were hard and poking up against my gown, he started flicking them with his finger. It didn’t hurt at all, actually it felt kinda good.
Dragging his ass off of my face and dropping to his knees, one of his hands grabbed my forehead and pushed it back against the bed. Two fingers from his other hand were stuffed into my mouth, he pried my mouth open as wide as it would go. My body thrashed on the bed as I feared he would break my jaw.
He positioned his saliva covered cock in front of my mouth and rammed it in. All I saw was his ball sack flying right at my eyes. Even more of his cock went in this time than before.
After withdrawing, allowing me to gasp for air he stated, “You’re a cock sucker now. You aren’t even fighting it. Your cock is hard, hell you are enjoying this! Just relax slut, I am about to face fuck youâ€¦ just relax.”
Without hesitating he drove his cock deep into my throat, his balls slapped against my forehead. Every muscle in my body tensed and I thought I was going to pass out. He quickly pulled out until only the head was between my teeth.
For a split second I considered biting the head off, I was too slow, he wedged open my mouth with his hand and thrust forward, his cock was deep in my throat before I could react. Being in that deep, with his balls resting against my nose, I was in danger of suffocating. Pulling out quickly, letting me gasp for air, then opening me up and driving it in again.
I must have lost consciousness at some point. Completely blacking out, until I felt my own orgasm quickly approaching. My head cleared and I opened my eyes, he was still fucking my mouth, his ball sack slapping against my face faster than ever before, my body grabbing quick bursts of air when he pulled out.
The most apparent feeling was his throbbing cock sliding along my tongue and into my throat then back out to be repeated again and again and again. The odd thing was the pain and fear had left my body.
My mind cleared a bit more and I felt my very hard cock being jacked off. Concentrating I located both of his hand still on my head. Following my arms, I found it was me! Oh my god! I was jacking off while this psycho orally raped me! I was enjoying this!
Even as my mind ran wild sorting out my thoughts, my hand flew up and down my cock. Even above the wet, flesh against flesh sounds of his cock sliding in and out of my throat, I heard the wet rhythmic sounds of my own jacking off.
For a reason I cannot explain, when his cock was about to be driven back into me, I sealed my lips around it and sucked as hard as I could.
“Mmmmmm, that’s a good cock sucker.” He paused for a moment, enjoying the feeling, then pushed forward until he was balls deep once again.
Just as his balls slapped my face, I felt my own sack tighten up, my back arched, opening my mouth as wide as I could and kept it there, I came. Not just any orgasm, this was “fireworks before your eyes” orgasm. I truly saw stars as spurt after spurt of cum splashed on my chest and stomach.
Even before I recovered from my own orgasm, his cock was out of my mouth and pointing right at my face. Staring at that cock as he jacked it off, all I could do was moan.
After only a few strokes, I saw his leg muscles tighten, before I could change my line of sight, a warm shot of cum stuck my chin with amazing force.
He leaned forward slightly as the next blast hit my right cheek. The final load hit the bulls-eye, right in my mouth, caking on my tongue and dripping down on the roof of my mouth. The salty creamy liquid was my reward.
He quickly pulled out and stood up, turning to my dinner tray, he squeezed the last few drops out into the soup I had ordered for dinner.
Gathering his clothes, he sat on the chair and got dressed, checking his appearance in the mirror before turning to me and saying “Good job cock sucker. I’ll be at your door same time tomorrow. Be dressed and ready. Maybe I’ll bring a friend or two.”
“Okay.” Was all I could mutter. Knowing I wouldn’t be changing hotels after all. I pointed to the five dollar bill on the floor and said “Don’t forget your tip.”