House Sitting Ch. 05

Jack and John

I found my way down the hallway to the master bedroom, casually strolling in my nakedness. It was strange being naked in Bill's house. I had often hung out with Bill but never in this way and never with Jasmine. This new freedom gave me a sense of confidence (or was it arrogance) that felt great. I wanted to be naked all the time.

The hallway was long and filled with floor to ceiling windows that looked out over the immaculate back yard, which was complete with an in-ground pool, hot tub, putting green, and outdoor kitchen. Following the southernmost edge of the house, I finally ended up in the master bedroom. The room was huge with an open floor plan while at the same time private and secluded from the rest of the house. The double doors separating the room from the hallway were open so I walked in and began to make myself comfortable.

Like the hallway, the far end of the room was comprised completely of glass windows and a set of sliding doors that opened out to a separate patio. There was a rather large raised bed to the right as well as a separate bathroom and walk in closet.

To the left was a small but state-of-the-art workout area and another viewing room complete with 60-inch television, Xbox, and computer. In the middle of the master bedroom in the floor was an 8 foot round section of glass. This was set apart from the wood and carpet flooring that made up the rest of the room.

I walked over to get a closer look and noticed the glass actually covered an in-floor hot tub! The dim ambiance lighting made it difficult to see how the floor opened up. I looked around and saw a series of switches on the wall by the double doors entering the room. I flipped each switch until, sure enough, the glass retracted under the floor revealing an inviting hot tub big enough for six people.

The thought of a hot soak seemed very inviting and hey, I was already naked! I lowered myself into the 102 degree water and let the heat and bubbles work their magic on my tired muscles. I closed my eyes and laid my head back to take in the relaxing moment. The water jets and bubbles massaged my body.

For the first time since entering the master bedroom I noticed there was music playing. The calming and seductive voice of Sade relaxed me even further to the point that I dozed off into a restful sleep.

I opened my eyes uncertain as to how long I had been asleep. The hot tub's jets and bubbles were still massaging my naked body and the water was still nice and hot. I looked around to see if anyone else was in the bedroom with me. I noticed it was still dark outside as evident from the windows showcasing the patio and back yard.

I had been in the hot tub long enough and pulled myself out and sat on the edge of the floor, my legs dangling in the hot bubbling water. I glanced at my crotch and had to smile. It never ceases to amaze me how sitting in a hot tub relaxes my manhood. Limp and relaxed, my penis must have been a full seven inches long and my sack hung like it weighed five pounds. I stood up and headed toward the bathroom, my man junk swinging as I walked. I found a towel in the linen closet next to the bathroom and proceeded to dry off. As I walked out of the bathroom something caught my eye.

There, tucked under the sheets of the bed, was someone sleeping. Were they there this whole time? Did I not see them due to the dim lights? Was it Bill? I quietly walked up to the bed and focused my gaze on the body.

I was on the opposite side of the king size bed. Whoever it was they weren't moving. The person's back was facing me. Just then I remembered what Jasmine had said to me earlier that evening in the kitchen. She must have finished with Shelly and come to the master bedroom to see if I needed anything. She must have seen me resting in the hot tub and, not wanting to disturb me, just crawled in bed and went to sleep.

Feeling relaxed after soaking in the hot tub, I gently pulled the sheets back and crawled underneath, making my way toward the sleeping Jasmine. I felt my way in the darkness until my hand touched the warm skin of the naked sleeping beauty. Her black curly hair covered her face as she slept. With my hand I gently followed the profile of her naked body from her hip upward just below her shoulder. I couldn't help but notice something about her body seemed different.

I moved closer, while on my side, until my own naked body was spooning hers, my cock gently pressing against her backside. I kissed the back of her neck and took in the coconut scent. I whispered 'good night' as I closed my eyes and fell fast asleep next to Jasmine.

I awoke some time later due to the sunshine coming in from the large windows that faced the back yard. The clock on the nightstand read 10:00 AM. Jasmine was still laying on her stomach asleep next to me, her face hidden in a pillow.

My morning hard-on was in full swing as I stretched and yawned from a restful night of sleeping. The sexual fun from the night before had really been exhausting. Pulling the sheets over my head, I leaned into Jasmine to kiss her naked backside. I gently touched her soft skin trying to entice her into finishing what we started in the kitchen the night before.

Jasmine moaned lightly as I gently kissed and touched her. I felt Jasmine move slightly. She reached her arm out from under the sheet and pushed a button on the remote control sitting on the nightstand nearest her. Suddenly the bedroom was completely dark as the black-out curtains shut blocking the mid-morning sun from view.

My eyes began to adjust to the darkness as I felt Jasmine's hand begin to tease my hard cock. Her touch felt electrifying as she began to stroke my shaft and squeeze tightly. This was beginning to be a great day already.

I laid on my back while Jasmine crawled under the sheet until her face was once again in my crotch. I closed my eyes and folded my hands behind my head enjoying the attention. With her hands and mouth, she expertly sucked and stroked my manliness. Her hot, wet mouth tasted my cock from tip to sac. Her lips wrapped around my balls and sucked them with amazing force.

I moaned with satisfaction as she continued my morning blow job. The louder I got the more eager she seemed to get. Her hand gripped my shaft with surprising strength as she stroked it. I wanted to watch as she pleasured me so I threw the sheet off the bed. Unfortunately, the room was too dark to see her in action. My eyes could only make out her head bobbing up and down as she sucked me off.

She sat up and crawled toward the night stand. I thought she was going to open the curtains but instead Jasmine opened the drawer to grab something. Without saying a word, she returned to her position between my legs. I heard the "pop" of something being opened. The scent of cherry lube entered my nostrils just as the cool gel covered my penis. Her strong hands rubbed my shaft and cockhead completely coating me.

Still grasping my cock, my silent lover turned around so that her back was facing me as she sat on top of me. She rubbed the head of my penis along her ass guiding me to her tight anus. My lubed cock head pressed against her tight ass as she leaned back onto me, forcing me inside of her asshole. Once my cockhead penetrated her tight asshole, she let go of my penis and balanced herself with her hands on my knees.

My erect penis slowly inched further and further into her ass. The gel lubricated my shaft allowing her to take my entire cock into her vice-like anus. Her ass cheeks rested on my thighs as my full erect cock filled her anal cavity. The sensation was overwhelming. I reached out and grabbed her hips with both hands. She flexed her hips and slowly lifted her ass upward. Her tight ass massaged my penis in a way I had never experienced before!

We continued in this way while both of us moaned and gasped in ecstasy. I knew I wouldn't last long before cumming. Her tight asshole was more than I could handle.

"I can't last much longer Jasmine!" I cried out. "I'm going to cum inside your hot ass."

At that moment she spun around on top of me, my cock still buried deep inside of her, so that she was facing me. She picked up the pace and started bouncing up and down as my penis impaled her ass. In the darkness, I could still only make out her silhouette. I noticed she was doing something with her hands near her crotch. Instead of fingering her pussy, it looked like she was stroking something, like she had a dildo or a vibrator.

I stretched my arms across the bed as I began to cum. My hand hit the remote control for the curtains and instantly sunshine filled the bedroom.

My eyes locked onto the naked person on top of me whom I had been fucking for the last half hour. She was stroking no dildo or vibrator. She was no she at all! She was a him and he was stroking his own erect cock while mine was buried in his ass!

It was too late to pull out. My orgasm was in full swing as I began to cum inside of his tight ass. He too was ejaculating as cum started spewing from his cock onto my chest and face. I was completely shocked and at a loss for words. My mind was saying no but my body was screaming hell yes! My cock unloaded cum in his ass filling it to capacity while my chest and face continued to collect his sperm.

As my mind was racing with thoughts of what was happening, my eyes locked onto his trying to make sense of this. Who was this person? Why didn't I realize sooner that this wasn't Jasmine? Was I gay? Why didn't I throw this guy off of me and beat him senseless? Time seemed to stand still as we both laid there looking at one another.

I broke my gaze from his in order to look more closely at his body. He was quite feminine in his appearance. His body was petite and shaved like a woman's body would be. His hands and feet were small and manicured. His legs were long and smooth. The only thing male in appearance about this person was his penis.

His small hand was still expertly stroking his own shaft. For his petite frame, his cock was rather large, appearing to be around 8" long and fairly thick. I found myself staring at his cock while he stroked it.

My own penis had gone limp inside of him. I made a mock-attempt at shifting my hips in order to see if he would get off my lap. Ironically enough I didn't feel embarrassed or ashamed. I was surprised and shocked but the longer I laid there the more right this moment felt.

"So do you have a name?" I asked in my deepest man voice, attempting to sound as macho as possible under the circumstances.

"My name is John. I work with Bill. I guess you could say I am his butler and friend." the naked man answered as he reached up and took the curly black wig off his head, tossing it onto the bed.

"Well I'm Jack," I replied. "Bill and I are friends from college. What's the deal with the wig?"

"Honestly, I am a bit embarrassed to admit this but..." John began to speak as he slowly lifted himself off of my lap. My limp penis slid out of his ass followed by a generous stream of cum. John was on his hands and knees straddling me as cum seeped out of him, running down his inner thigh and dripping on my crotch. His face was inches away from my crotch and I could feel his breath on me.

John continued talking as he gently touched my cum-covered penis.

"I saw you yesterday in the viewing room before Shelly joined you. I watched as you masturbated in front of the television." John stated as he slipped a finger in his mouth tasting my salty semen.

"If I had a dollar for every time I've done that myself, I could retire by now." John added. "Then I watched as Jasmine explored your nakedness in the kitchen. I could barely keep myself from running into the kitchen and sucking you off right then and there." John continued explaining as he placed his mouth on my limp cock, licking my shaft and rubbing his lips on my manhood.

"When I heard Jasmine tell you where the master bedroom was located, I rushed back here to hide and see if I cloud find a way to enjoy a piece of you for myself." John stated while still toying with my genitalia.

"While I was in the closet, I found this black wig and it hit me - why not slip into bed and pretend to be Jasmine?" "I was hoping you wouldn't be able to notice my disguise in the darkness." John said with a wink and a smile.

"When I awoke this morning to your kisses and touch I couldn't resist myself. I hadn't planned on both of us falling asleep and I was worried you would see that I wasn't Jasmine in the daylight. That is why I closed the curtains to make the room dark in hopes of fulfilling my fantasy Jack."

"The feeling of your cock deep inside of my ass was amazing! Did you enjoy fucking my ass Jack?" John mumbled, my hardening cock deep inside his mouth.

John let my penis escape from his lips as he looked up at me for a response. I was speechless. I didn't know what to say. I had never in my wildest dreams considered fucking another man in the ass, not to mention allowing him to suck my cock afterwards! I must have looked like a mess with John's cum all over my chest and face.

"I think I need to clean up." I said as I managed to compose myself and sit up on the bed.

I grabbed the towel I used earlier and began to wipe John's cum from my face and chest. Suddenly I had an urge to taste what it was like. I placed my tongue to the towel tasting John's cum. The salty sperm was interesting and not entirely disgusting.

I finished wiping myself off and looked back towards John. He sat on the edge of the bed looking at me. John's cock was still extremely erect. The image of him on top of me as my hard cock was buried in his ass was all that I could think of.

"I thought you were Jasmine." I said trying to make some sense of what just happened.

"I know," John replied. "That is what I wanted you to think Jack. How else was I going to get to feel your big cock shoot cum inside my ass?"

"I can't say that I wasn't turned on at the thought of fucking Jasmine's ass." I began to explain. "I guess I never thought I would have sex with another man. It never crossed my mind."

"Look" John said as he stood next to the bed, "Just because you had your dick in my ass doesn't make you gay. Can't two consenting adults enjoy each other without being labeled this or that?"

"That would be nice for a change." I agreed as I looked over John's naked body, admiring his still very erect, large penis.

"Are you up for a swim John?" I asked as I stood up. Not waiting for an answer, I opened the patio doors and walked out to the back yard. The warm air and bright sunshine energized me as I looked around and took a deep breath.

Standing at the edge of the pool, I could see houses in the distance through the wooded acreage. There was no fence marking the property, only trees and foliage. I could barely see the neighbors and hear their voices as they too enjoyed the beautiful summer day. The nearest house was nearly 100 yards away so it was doubtful anyone would notice my lack of clothing.

My quiet moment was brought to an abrupt close when I was tackled from behind by John as we both fell into the cold refreshing water.

I stayed under water for a minute letting the cold water cleanse me. The cool water felt exhilarating against my naked body. I surfaced and started swimming toward the diving board. John was splashing around like a kid at summer camp, going on and on about how much he enjoyed swimming in the nude.

"Cannon ball!" I yelled out as I landed in the water a few feet from John. The wake of water sent him flailing into the shallow end. We both swam in the pool for a while enjoying the sunshine and being naked outdoors.

John was standing in the pool with only his head sticking above the water. I swam up behind him and returned the favor from earlier by grabbing his legs and dragging him under the water. We both surfaced laughing and catching our breath.

We splashed each other and wrestled in the water. We both tried to water-log one another by jumping onto each other from the diving board. It was sincerely fun and light hearted.

I was floating on my back when John started to laugh out loud.

"I see there is some truth to cold water and shrinkage" John teased as he pointed at my limp penis. I looked at my package to see what he meant.

"Don't you worry yourself about that Johnny boy," I replied. "The warm sunshine will take care of that."

I swam over to the edge of the pool and pulled myself out. I sat on the decking with my legs dangling in the water. The warm summer air felt good on my skin. Before long the sunshine warmed up my body back to normal, not to mention my manhood.

John grabbed a couple water bottles from the outdoor kitchen and joined me as we sat side by side by the pool. We both talked freely about the experience we just shared and our lives in general. John was somewhere around the age of 30. He seemed very cordial and professional as we conversed. Astute and one for details, John kept himself in shape by swimming daily and training for his next marathon. John was clean shaven on his face, and from what I remembered from my earlier interaction, completely hairless on the rest of his body.

John and I sat together and talked like old buddies. We actually had a lot in common. We talked about Bill and his freelance work as a film editor. We joked about all the women who came in and out of Bill's "love nest".

John had a few hilarious stories that he shared with me. I finished my water and lowered myself back into the pool. I took a deep breath and sunk below the water's surface. The cool water was refreshing as the outside temperature continued to rise.

As I re-surfaced, I noticed John sitting on the edge of the pool, his legs spread wide. It was hard not to notice his rather large cock and shaved crotch.

"So John," I asked matter-of-factly, "do you normally pretend to be Jasmine in order to get strange men to fuck you in the ass?"

John laughed at my direct question. "I was wondering when you were going to ask me about that Jack. I consider myself more of a metro-sexual, I guess." John replied.

"So does that mean you fuck girls AND guys?" I asked curiously

John pondered the question before answering. "Yes and no. I get turned on by beauty. If a beautiful woman or attractive man catches my eye, I see if they are interested in having some fun. I am no more gay than you are, Jack."

"Well I can see your point of view John." I said in agreement. "But you have to admit that the way you tricked me into thinking you were Jasmine was a bit deceiving."

"Yeah, that was indeed a bit deceptive Jack." John agreed. "So if I walked up to you and said that I thought you were attractive and that I'd like to feel your cock in my tight ass...would you have fucked me?"

"Probably not!" I said chuckling. "But it was an interesting experience John. One that, until earlier today, I would have never considered."

I swam around for a bit and once again sat on the edge of the pool next to John. I looked over at John who had one leg stretched out across the pool decking and the other still in the pool. In this pose his crotch was wide open to my line of sight. His hairless body looked strangely attractive.

"So do you shave your entire body? That would seem like it would take a lot of time?" I asked John.

"I had my body hair removed to help with my swim time in the water. Another great side effect however is how amazing it feels to be hair-free all over!"

I had to admit, his man junk looked clean.

"Here, feel for yourself," John said as he motioned for me to handle his hairless crotch. "Don't worry Jack, nobody will know. And besides, it's not like you don't have the same tackle as me, right?"

What could happen that hadn't already, right? I mean an hour ago my dick was buried balls deep in his ass and he was sucking and licking me like a professional whore.