House Sitting

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House sitting my brother's house with my friend John.
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tonyl65
tonyl65
2,352 Followers

I was house sitting for my brother. I didn't want to be alone so invited my friend John to come stay with me. We hadn't seen each other since we graduated high school. It was hot in July, really. It was getting late and we just had on some very short shorts and tank tops, it was the late 70's. We started playing poker. Money was going back and forth getting boring. I suggested we play for "truth or dare or slave". Slave is when you have to be the person's slave for 5 minutes and do whatever they are told to do.

I won the first hand and John picked dare. There was a party going on next door and the houses were separated by the long driveways that ran up along the houses and running to the back to the detached garages. Their driveway was lined with cars and ours only had our two cars. I dared John to take off his shirt and walk out the front door, up the driveway, and around the back of the house to the back door, letting the neighbors see him half naked. He did it as he walked slowly up the driveway.

About halfway up the driveway he was strutting and shaking his ass at the neighbor's window.

It was getting dark so they couldn't see much. The next hand John won and I picked truth. He asked if I jacked off and tasted my cum, I told him yes, all the time.

Next hand he won again and I picked dare. He dared me to do the same thing that I made him do, but naked. I leaped up and dropped my gym shorts and pulled off my top. Then I pulled down my underwear and flicked them off my foot, right at his face. John grabbed the underwear off his face but held onto them. I went out the door and stayed in the shadows of the house. I didn't crouch down but I walked quickly until I was alongside of our cars. I slowed the pace glancing into the neighbors windows. Nobody even looked my way. I went back into the house. John laughed and tossed me back my clothes. I slipped my gym shorts back on but left my underwear and shirt off.

I won the next hand and John picked slave. I told him I wanted a back massage for 5 minutes and it had to be on the bed so I can relax. We went into the bedroom and I lay on the bed. John began to rub my back, it felt good but he stuck to just my neck and back. When the timer went off we went back into the living room. John had a major hard on tenting his shorts.

I lost the next hand and John wanted a massage to. We went back to the bedroom and John turned off the lights saying he wanted to relax. It was now pitch dark, hot, and humid in the house. I waited a second or two for my eyes to adjust. The drapes blocked out most of the moonlight. I got on the bed waiting on my knees. I could see John's silhouette as he pulled off his shirt. He then crawled onto the bed. I started to rub his back. Then I moved down to his legs. He was moaning as I rubbed his inner thighs. I ran my hands up his legs and didn't stop as I crossed over his ass cheeks, then up his back. He was moaning to let me know he was enjoying his massage. The timer went off and I slapped his ass "all done" I said with a little laugh.

The next hand I won and John picked dare, again. Damn I thought, no I hoped that he would have picked slave. I dared him to go outside naked and walk on the other side of the cars next to the neighbor's house. He turned white, but stood up and pulled down his shorts. He went to the door and I watched as his ass clinched a couple of times. I ran to the side window and watched as he walked up the driveway. Just as he passed the first car the front door opened up and a couple was leaving. John ran up the driveway and through the back gate on my brother's house. I was cracking up. He walked into the living room with a major hard on. He grabbed his shorts and slipped them back on. We both were cracking up.

I lost the next round and picked slave again. John asked for a full body massage since he just ran outside. We went back to the bedroom and I told him to take off his shorts because they just get in the way. He turned the lights off and I heard him drop his shorts. He got on the bed and I quickly dropped my shorts and followed him.

The lights were off so he could "relax" so he didn't even know I was naked as well. I started to massage his neck and back and work my way down. I massaged my way down towards his legs and grabbed each cheek of his ass and gave them a couple of nice squeezes. He moaned and flexed his ass. I continued down his legs to his feet.

I started back up his legs and he spread them wide for me to rub his inner thighs. I was able to go all the way up until I felt his soft, warm ball sack. I used the back of my hand to rub his balls as I kneaded his thighs. He was moaning and actually lifted his ass a bit to give me better access to his balls.

I thought it was now or never so I grabbed his ass with one hand and started rubbing and kneading his ass cheek. I then grabbed his balls with the other hand and massaged his balls. His legs were so far apart I had access to his tight hole. I used my thumb to start rubbing just past his balls as I worked my thumb up to his hole.

When my thumb touched his hole he moaned and pushed back against my thumb causing it to put more pressure on him, "Does that feel good John? You like this massage?"

John was a whimpering baby right now as he lifted his ass up some more and pushed back hard against my thumb, "Oh god yes. Don't stop, please." His voice was pleading.

I told him to roll over onto his back so that I could give him a frontal massage. He didn't hesitate, he flipped onto his back. I grabbed his balls and began to massage them some more. Then I wet my finger, on my other hand, and pressed it to his hole. John lifted his legs up to his chest offering me his tight boy pussy. I leaned my naked body against his, letting my hard cock press between his ass, and forcing my hand tighter against his hole. My finger pressed into him, right up to the second knuckle. John let out an erotic moan.

I grinned knowing I had him right where I wanted him, "Oh ya, that's what you want now isn't it? Your tight little pussy needs a little attention."

I leaned forward pushing more of my finger deeper into him as I ran my tongue up his shaft. I felt the hot warm tissue wrap around my finger. I felt the hard nub of his prostate as I wiggled my finger against it. I found a large drop of precum ready to drip from his head. I flicked out my tongue and licked it off. "Oh you're liking this a lot. You want me to do more?"

John grabbed himself behind his knees and pulled them to his chest, "Please..." he whimpered. His head whipped back and forth as he fought the sexual desire for more.

I massaged his warm spongy walls of his anal canal, "Please, what? Please, stop? Please, what John?"

John's ass muscles were flexing around my finger, trying to draw more of it in, "Please...please..."

John was rotating his hips against my hand, moaning in pure ecstasy. I took his cock and sucked it down my throat. John's body tensed. I could see him grab handfuls of bedding as his muscles tighten trying to hold back his orgasm. I circle my tongue around is soft spongy head, dipping my tongue into his cum dripping hole. I lifted my head up, "Does that feel good baby? Do you want me to stop?"

John was arching his back and pressing his cock into my face. His hip didn't know whether to push his cock back into my mouth or fuck against my finger. He was a gyrating mess of whimpers and moans. His cock continued to jump and pulse as he flexed his body tight. I lightly kissed his balls and nibbled on the soft fleshy. Grabbing his ball sack with my teeth I gently pulled his balls away, stretching his sack. The skin on his cock became tight as more cum dripped from his head.

John screamed out "Oh god yes, that feels so good...I'm going to blow."

I backed off and let him calm down as I gently kissed around his cock and chest. I tried not to move my finger but still kept it firmly planted in his ass. I didn't want to push him over the edge yet. I moved my body up his and kissed his neck. I worked my way to his ear. My cock was even with his and I let my weight fall on him, our cocks smashing into each other.

I used my tongue to run along his ear lobe. I whispered into his ear, "Tell me what you want John?" then I slowly nibble his ear lobe.

As my teeth bit into his ear he screamed out, "Fuck me. I want you to FUCK me."

I pulled my finger out of his ass as I moved my body back down his. My face was over his throbbing cock. A puddle of precum filled his bellybutton. I dipped my tongue into the warm liquid and swirled around the hairy filled hole. I put my lips against his stomach and sucked in the liquid gold. It was so sweet tasting. I moved my mouth to the tip of his cock and licked the drop of cum before it fell. I lightly ran my tongue down his shaft, across his ball sack, and continued down.

I grabbed his cheeks and spread them as I inserted my tongue in his hole. John let out a deep grunted "YES, Oh god Yes!"

I got his pussy nice and wet. I spit in my hand and lubed my cock. I knelt up between his legs and placed my cockhead to his hole, "Are you sure you want this?"

John looked at me "Fuck me please. I want to feel your cock in me."

I pressed my cock forward and let it slip in. John grunted deep in pain but I felt him push and wiggle his ass against me trying to get more in. I pulled back a little and pushed forward some more. My cock head slowly stretched his sphincter muscle until my head popped past the tight ring. I froze while his body adjusted. "Are you ready for more?"

John was wiggling his ass trying to draw in my cock, "Give it to me. Make me your lover and fuck me."

I let me body weight fall on him forcing my cock deep into his ass. I rocked my body forward burying my cock deep into his hot ass. Our faces were nose to nose. "You're mine now. My cock is deep inside you and I'm going to fuck you. Is this everything you dreamed of John? Do you like having a cock inside your boy pussy?"

John looked at me, his face was perspiring as his body adjusted to my intrusion. He reached up and grabbed me around my neck and pulled me into a deep kiss. That was the signal I needed to begin fucking my new lover. I pounded him long and hard. I lifted back up and started to really give him a long ride.

John screamed out as his cock jerked up off his body, his cockhead flared out, and he shot his cum all over his neck and chest. Streams of hot white cum splattered against his skin. His ass muscles tightened around my cock, squeezing tight. I pushed through his orgasm as I continued to fuck him. His cock continued to bounce and jerk as his thick cum dribbled out the tip.

I leaned forward and licked some of his cum from his chest and neck. I pushed my cock deep into him and started to release my own seed deep inside of my new bitch. I drove my cum covered tongue into John's mouth as my own cock flexed inside of him as my cum filled him. He was mine.

tonyl65
tonyl65
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8 Comments
AnonymousAnonymousabout 4 years ago

A good enough story - but really, what is a boy pussy? A truly gay man would want nothing to do with a pussy! He wants a nice, tight ASS, and that is what he would call it!

AnonymousAnonymousover 6 years ago
Were You There?

This is really scary! Some of the details remind me vividly of my very first sexual experience, with my 8th grade teacher. PLEASE ... MORE!

AnonymousAnonymousalmost 7 years ago
My first time

Reminds me of my first time. I was house-sitting my next door neighbor's house and I invited my BFF to cum sit with me. We winded up on the carpeted floor of my next door neighbor's daughter's room in a 69 sucking each other's cock feet away from where I parents and family were mulling around. He could have easily turned me into his cock slave once his cock hit my lips! Loved it and still love cock like the very first time!

Indiscreet1Indiscreet1almost 8 years ago
So sweet!

Thank you! What a delicious story of first fuck. I love the way he makes John say what he wants, what he really wants, that stiff cock deep in his ass. Ummmmmm.....

SusanlynnSusanlynnalmost 8 years ago
Ohhh myyyyy

DAMN, I want to be John so fucking bad!!!! I can't wait to read this to my husband. He's going to rape his little sissy faggot wife and I can't wait!!!!

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