I have been staying at the same hotel, every Sunday through Thursday, for over a year. Work takes me to this place and stresses me every single day. My nights are my only respites and I try to take every advantage possible.
While I always sleep in the nude, unfortunately, there is not any good way for me to take walks outside in the same manner. The hotel is in a rural area near an airport, surrounded by trees on three sides and a fast food restaurant on the fourth. Beyond the trees are a railroad and a truck depot. If there was a clearing in the wood without sightlines from anywhere, I had never found it on any of my nightly walks.
What I could do however was to wear a pair of very thin silky jogging pants that are about two sizes too small and a pullover silk shirt. I get very close to feeling naked without the legal issues of being that way when and if someone was looking. Under this, I usually sported an elastic cock ring. Together, my outfit and the sensation of being in my desired state of nakedness got me and kept me swollen with cock felt pride.
To date, there have been a few women who have stared at me from their windows, taking in the sight of my pronounced hard-on bulging in my pants. Once, one of the female staff members, a cute rail thin wisp of a woman, stopped the hotel van on her way to the airport to speak with me. With hands on hips, I stood facing her but kept my head turned looking toward the highway while we spoke. Each time I glanced back at her, her eyes were transfixed on my crotch.
I truly love being looked at and enjoyed every second of exhibitionistic thrill. I hoped that she might knock on my door one night, but she never has. I am sure she would have been a lot of fun. Other than that one time, nothing has ever happened to interrupt my solitude. Until last night.
I was on my normal walk, enjoying the cool evening air. Finished with being clothed outside I was on my way back to my room to strip down and feel free. I noticed the curtain of the room next to mine moving. Either the occupant had just closed it or they just did not want to be seen. I decided to stay where I was for a little while and lit another cigarette. Facing the building, I looked up and down the three story building, which is under renovation, half studying the progress of the work, and half watching for the curtains to move again.
They did move again. There was just a sliver of light coming from the one side with the light obstructed just a bit by a head. I could not make out whether my viewer was a man or a woman, but I decided to finish my smoke and hoped it was a woman and that she would open the curtain a little more to allow me to see her too. But, no such luck.
When finished, I flicked the butt into the sewer grate and began to walk. As I reached the door, I fished out my key card. Just as I was about to unlock the door a beautiful young woman appeared on the other side coming out. She was drop dead gorgeous. A black haired, black eyed beauty with a smile that lit my heart. Her lithe, well endowed frame was covered only by an ultra short thin cotton sleeveless shift. Elastic held it above her breasts but did nothing to conceal her bountiful bosom.
“Are you finished with your walk already?” She asked as she pushed open the door.
I held the door open for her and sensing she was looking for company said in reply, “I was, but I don't have to be.”
“Good, I hate being cooped up inside with nothing to do and I'm going to take a walk of my own. I was hoping you might like to walk with me.”
“It would be my pleasure,” I said as we began walking.
She initiated our conversation by asking me what brought me to Milwaukee. I told her all about my job and how long I had been there. She asked all the right questions as I progressed through my narrative and then I asked her what she did for a living and what brought her to this place.
“I'm a marketing rep for a pharmaceutical company. This is at the far end of my territory and I have about two dozen doctors to give samples to. It takes me a couple of days to get to them all and it's just too far to drive from home each day, so I stay here.”
“Do you always stay at this hotel?” I asked.
“Yep, this is the third time I've stayed here that I've seen you taking your nightly walks. It's been just over a year that you're staying here, isn’t it?”
“You're right, it is just over a year that I've been here. I've never seen you here though. Believe me, I would remember.”
“Normally I just stay in my room and veg out, but I decided that tonight I wanted to shake things up and do something a little bolder than normal.”
“So your idea of being bold it to take a walk?” I asked with a chuckle.
“That's part of it,” she replied leaving the rest of her boldness decision open.
“What's the rest of your plan to be bold?”
“Did you ever think that… you do know that people see you walking out here, right?”
“Of course I do. That's why I'm wearing clothes.”
“And we can all see your, um, we can all see just about all of you?”
“Sure I do. You know that I can see just about all of you too, so what's the difference if you can see more of me as I leisurely stroll than what you would normally see in the office? I'm sure you don't wear that shift to the doctors’ offices.”
She smiled warmly at me and said I was right. I interrupted the flow of the conversation by saying, “You were saying are a rep for a drug company. What do you sell?”
“I specialize in urology, but my rounds take me to GP’s as well. I keep them informed and give them samples of our E.D. medication. You know, erectile dysfunction. You don’t have a problem in that area though, do you?”
“No,” I laughed, “I don't. And I believe that any red blooded man in your immediate vicinity wouldn't have that issue either. But that doesn't stop me from wondering if those little blue pills really work.”
“Oh, they work alright, and thank you for your compliment. On a healthy man like you, they would keep you erect even after you've ejaculated.”
“Gee, that’s a very clinical way of saying it.”
“Sorry, when I’m talking about that stuff, I just kind of fall into doctor speak. How’s this, for a guy like you, you’ll stay hard even after you cum and you’ll be able to keep satisfying your woman.”
“That sounds much better.”
“So, are you always semi-hard like that?” she asked nodding her head toward my crotch.
“No, to tell the truth, when I take my walks like this at night, I wear a cock ring.”
“Ah, that says a lot.”
“Does it? What does it say other than I’m wearing a cock ring?”
She responded, “Well, it tells me that you like people to look at you, you don’t mind them seeing you excited like that and that you certainly aren’t shy about yourself or your language.”
“My language?” I asked.
“Not many men would say cock to a woman they just met.”
“Okay, I see what you are saying, but it would just plain weird to say penis squeezer.”
She laughed at my terminology and reached for my hand.
“Do you mind?”
“What, holding hands?”
“Yeah, do you mind?”
“Not at all. In fact, I like it, I like it a lot. You have very soft hands.”
“Thank you. Have you ever tried one?” She asked.
“Tried one what?”
“Tried one of our little pills.”
“No, I couldn’t see going to a doctor, paying the copay, and then paying for a prescription just to try it on myself.”
“You’d be trying it on your woman, not on yourself,” she said smiling at me.
“If I had a partner, a woman, I might have tried, but I don’t so I haven’t.”
“If I gave you one, would you take off that ring and try it?”
“You can do that, just give one to a stranger that you don’t have a medical history for?”
“Well, you’re right, you would have to be very closely monitored. Besides, we’re not strangers, we’re holding hands.”
“Well hi person holding hands with me, my name is Bill. What’s yours?”
“I’m Amy. That wasn’t too difficult was it?”
“No, it wasn’t.”
“So, do you want to try one?”
“As long as you monitor me personally and as closely as you possibly can.”
“I do believe that it would be my great pleasure to do just that.”
We were near the entrance to the building by that time, so I got the key card out as we approached the door. After unlocking it we entered and both turned down the same hall. Amy stopped at her door, next to mine, and used her own key card to open it.
“I thought I saw someone at your window earlier,” I said as I unlocked my door.
“Yeah, that was me. I think I enjoy looking at you as much as you enjoy me looking at you. Why don’t you just come in my room?”
“I think I probably will cum in your room,” I said with a chuckle, “I thought I would just get cleaned up first. Besides, we have adjoining rooms, we can just open the doors.”
“Oh, yeah, right,” she said entering her room still laughing with me.
We both opened our doors and shut our hallway doors. I was about to turn and begin getting ready for a shower when Amy cleared her throat to get my attention and gave me one of those little wiggles of the finger to beckon me into her room. As I crossed the threshold, Amy took my face into her hands. She brought her lips to mine and gently kissed me. Just as I was about to open my mouth and introduce her to my tongue, she broke the kiss and backed away from me slightly.
“Bill, can I ask you a question?”
“On one condition. You answer mine first.”
“Okay, shoot,” she said.
“Why me,” I asked. “I’m easily twice your age, I’m not all that good looking, you are drop dead gorgeous and could have any man you want. You didn’t need to go for a walk with a guy like me. You don’t need to give me a cock stiffener and watch it work. Why me?”
Amy looked down and then back up. Her eyes met mine and she said, “I’ve watched you on two other occasions before tonight. I’ve been really horny since my boyfriend and I broke up and with this trip coming up, I saw a chance to kill two birds with one stone. If I could get the chance to talk with you, I figured I could talk you into showing me the cock I’ve admired for a while now and I could get myself off while you did the same.”
“So you want me to take a pill and then masturbate while you masturbate while watching me?”
“That’s what I thought at first, but after speaking with you, I would like to do more than that. Would you like to do more than just masturbate?”
“Amy, come on! I mean really! Who’s putting you up to this?”
“What do you mean?”
“A beautiful woman like you doesn’t have to be with an old man like me. You can take your pick of any guy your age in the lobby. Who’s putting you up to this?”
“Bill, I’m telling you the truth. To be blunt, I’ve craved your cock for a long time. If you don’t believe me, that’s fine,” she continued as she unlocked a suitcase and opened it.
“Take these, close the door and enjoy the rest of the evening.”
She handed me a box of pills and stood with her hands at her side. We looked into each other’s eyes for a moment or two.
“If you do believe me, answer the question I was going to ask you by taking one of those pills, get out of your clothes, take off your cock ring and let’s take a shower.”
Relenting, I opened the box, took out a sample packet, opened it and downed a pill. My shirt, pants and sneakers were quickly discarded. She lifted and peeled her shift over her head revealing to me that she wore nothing else to hide her magnificent body. In no time at all, we were both naked under the warm water of the shower.
With soap in hand, she washed my back, her soft hands sliding across my shoulders and down my arms. I stood still with my hands on the wall in front of me, wondering just how clean she wanted me to be. My curiosity was soon answered as her fingers delved deeply down the crack of my ass. I spread my legs and she cleansed me thoroughly outside and inside to her fingers depth.
I’m not sure how much was the pill and how much was me naturally, but she had my cock at full attention. She knelt behind me and washed my legs before standing and turning me around. She looked down and then back at my eyes.
“The pills don’t work this fast,” she said.
“Well then, it must be the stunning woman I’m showering with. The one with the magnificent breasts, the one who shaved herself between her legs, the one with the smile that would light any room, the one with the hands of an angel and the face of a million dollar model.”
Her hands went behind my head and mine went to her back as we pressed together. Our lips met and mouths opened. Our tongues played together in our saliva sandbox. What a joy she was. Open and adventurous, willing to be naked with a man simply because he had shown the shape and length of his schlong. My cock was pressed upright between our bellies, fully expressing my gratitude for her attentions.
She broke the kiss and began soaping my chest. Her hand made lazy circles across my skin while I took the opportunity to study her firm ripe breasts. Each was tipped with light brown slightly puffed aureoles and pencil eraser sized nipples. My mind raced forward, imagining having them between my lips.
As her hand found my stomach, I involuntarily gasped causing her to ask, “Are you okay?”
“Amy, this is absolute heaven!”
She went to her knees and smiled up at me before beginning to wash her way up my legs. She was leaving her obvious destination for last and best. Her hands gently soaped my balls and cock before she set the soap aside and she scrubbed me clean with delicious pressure. Once thoroughly free of soap she pulled my cock to her mouth and gently kissed me. She seemed to inspect my entire engorged cock with her lips and tongue. She took my cock in hand and began slowly stroking me as she took each of my balls into her mouth one at a time. The pleasure of her lips was intense. I felt her hand go between my legs and a finger began pressing into my ass.
“Oh god,” I sighed.
I looked down to see her hand grasping my rock hard cock, her tongue slowly licking my sack and her deep black eyes staring up at me.
“Amy, not yet, I don’t want to cum yet. Let me wash you first.”
It was her turn to relent. She stood and said, “Don’t worry about going soft, Bill. I guarantee you won’t.”
“It’s not that. If I cum now, I think I’ll faint. Jesus, your ex is a real ass for letting you get away,” I said picking up the soap.
I briefly kissed the lips that so expertly played with my manhood just moments before and turned her around. As she had done with me, I started at her shoulders and worked my way down her back. Passing her trim waist, I went to my knees and filled my hands with the cheeks of her ass. They were perfect. Toned and taut, the globes moved deliciously beneath my hands. Following her lead, I paid special attention to her ass hole too. She tilted her hips for me, showing me her yearning side. I had every intention to investigate her here with my tongue later on.
I stood and began to wash her chest without turning her around. Instead, I took her glorious tits in my hands. I washed and rinsed each of her perfectly shaped, soft yet firm tits as my lips and tongue played a symphony on the muscles of her neck. My cock pressed deeply into the crack of her ass. Her head fell back onto my shoulder and her hands covered mine, urging me to press and squeeze her, to tweak her nipples and pull on them. This is what she wanted, so this is what I gave her. She slowly moved her ass up and down my turgid cock, stroking me with her sensuousness.
Falling to my knees, I now turned her to face me. I wanted, no needed to see her shaved mound as I cleaned her folds. Following her lead once more, I started at her ankles. No time was wasted unnecessarily on my journey up her legs and soon the folds of her pussy were in my hand. I opened her and cleaned every nook and cranny.
Now, with both of us clean, it was time to start playing in earnest. Her pussy was swollen with excitement. I dipped one finger into her depths and began by licking her navel, exploring her with my tongue. She took a long staggering breath and her hands came to rest on my head, pushing me lower. Heeding her request, my mouth trailed down her tummy as my finger continued to plunge deeply into her. Her clit rose to meet my lips. Her hands no longer played in my hair and I looked up to see her head thrown back and her hands steadying her on the walls of the shower.
I sucked her nubbin into my mouth and toyed with it like a miniature nipple. Her gasps told me all I needed to hear. Her nectar was sweet but sour at the same time. She was delicious. Too much water cascaded down her heavenly body for me to truly appreciate her real essence. Three fingers now explored where I hoped my cock would soon be and I found her trigger amongst the ridges inside.
“Oh Christ,” she called out. Words born amidst the moans of pleasure.
I found her ass hole and played the last string of the chord.
“FUCK,” echoed in the small hotel bath and she crumpled, saved from falling only by my arms.
Gently, carefully, I sat in the tub and lowered her into my lap under the constant rain of the shower. Her smile conveyed not only satisfaction but a peaceful bliss. Moments of silence passed while she regained her composure. We kissed leisurely and teased each other's lips. I couldn't help but admire and stroke her breasts, cupping and squeezing them as her nipples at first softened but then began to swell and harden again beneath my fingers. My raging hardon was trapped between us, nowhere to go and nothing to do other that remain almost painfully hard.
Amy lifted her foot and shut off the water and whispered in my ear, “Let’s dry off and go in the bedroom. I really think I should take a very close look at you and check for side effects.”
“Why thank you, Amy, you are most definitely the warmest medical professional I've ever met. Your tubside manner is, shall we say, astounding and greatly appreciated.”
After another quick but very sensual kiss, we climbed out of the tub, her tight little ass jouncing a bit as she took each step over the side. I took a towel from the rack and began drying Amy’s hair. She took a towel and as she pressed her body to mine dried my back. We kissed again, longer and harder than before. Both of our physical needs were beginning to boil. I was starting on her back as she moved from me slightly and dried my chest. This only lasted for a moment, for as she dipped her hands below my waist with the towel, the towel dropped and she took my blood hardened cock in her hands. Our lips met once again before she backed away, still holding me, and let me to the bed.
“I need it,” she said huskily as she fell backward onto the mattress.
I wanted to make sure she was thoroughly oiled up and primed for the pump, so I lifted her feet from the bed and nibbled on each of her toes for just a few seconds each. Then, spreading her feet, but not releasing her ankles, I began to kiss up the inside of her legs. Slowly spreading her wider and wider, sliding my hands down her willingly spreading legs, I approached her bald lips. They were swollen and waiting, but I was moving too slowly. She pulled my mouth to her cunt, pulling on my head with her hands and mashing me against her. She was already parted and my tongue slid easily in and out of her before I lifted and got to work on her clit.
“For god’s sake, stop teasing me and fuck me already!” She cried.
“Your wish,” I started as I climbed aboard, guiding my rock hard cock head to her willing cunt, “is my command.” With outstretched arms supporting me, I watched her face express blissful surprise as I easily drove myself into her very wet core. I withdrew and drove deeply, time and again, pounding her cervix with excited abandon.
“Holy Christ! You're so fucking big!” She shouted breathlessly.
“Cum on my big cock baby.”
“More, more, give it all to me.”
I did, repeatedly slamming eight inches of cock meat to the hilt. My balls slapped her ass until they began to well with expected release.
“I'm going to fucking explode!” I cried out.
“Give it to me, give it all to me. Cum in me, now, cum in me!”
I did. Pump after pump, I shot my load into my beautiful raven haired erection machine.
“I feel it,” she cried as I continued to pound her. “I feel it…. ugh… I feel…”
Her words turned to a high keening as her body began to tremble. Her eyes rolled in her head and her hands gripped the sheets as though she was possessed and about to be tossed from the bed. Her entire body shook as I continued my cock in cunt assault.
“Stop, st….” she managed as another orgasmic wave crashed her body.
I slowed, but did not stop. I inched my newly found stamina stabber in and out of her slowly, withdrawing until almost out and then gently back in until fully enveloped.
Her eyes opened and in a breathless whisper she said, “Shit, that was amazing.”
“Do you really want me to stop?”
“Yes, no, go in the bathroom. Get the lotion bottle.”
I did, thinking she was beginning to get a little sore. The bottle was right by the sink. Upon my return, I found my lovely on her elbows and knees, our mixed cum oozing from her onto the bed.
“Fuck me in the ass. I want you to fuck my ass.”
“I've never…”
“Just pour the lotion on your cock and on my butt hole and then fuck me.”
Generously lubed, my unwavering hard-on pressed slowly into her waiting hole. It took a couple of moments for her to relax enough for me to fully penetrate her, but once I was in, her tight ass, so warm and accommodating, gave us both pleasure almost beyond imagining.
I remained on one knee as I grasped her hips and began to fuck her the way she had so eagerly asked for it. She rubbed her clit and mashed her tits with her hands as our bodies crashed together. Still hard as a rock, there was no slowing me down. There was no urge to cum, just an animalistic need to fuck like crazy and enjoy every sense.
The first sign of her impending explosion was the trembling in her thighs. Her hands went to the sheets by her head and she again grasped on as though about to be thrown to the floor without the grip.
“FUCK!” She screamed loud enough for the entire hotel to hear.
She literally bounced on the bed as her arms and legs shot out in all four directions. My cock slipped from her ass as I lost my grip on her hips. I was left kneeling behind and above her moaning body. She rolled to her side, red faced and exhausted. My prick pointing at her face, still hard, coated with shit and lotion, and still ready for more action.
“If you wash up a little, I think I'd like to rest a minute and then take a short walk. Is that okay?” She asked.
“I would like that as long as we come back here and you monitor me some more.”
“Oh, Bill. I'm not letting you out of my sight all night. In fact, when we get back, I think I'll need to give you an oral exam.”
