My First Time

It was finally Summer and school was out. I was still living at home with my parents at least for a few months. Until I found a job or decided on what I was going to do?

I was doing odd jobs landscaping and mowing yards what ever I could do to make a little money.

I had been outside in our backyard talking to the neighbor. He was a older guy maybe sixty, a bachelor he had bought the place next to my parents house a few years ago. He was usually quiet and kept to himself, but he always seemed cool, always said hello and was friendly he was still a pretty good looking guy for his age.

He he was outside doing some yardwork when we started talking and he invited me over telling me to stop in some evening when I wasn't doing anything for a drink and then he asked laughing if I was old enough to drink. I told him as long as I don't get caught I'm only nineteen. He smiled and said stop over.

A few days went by and the weekend rolled around it was Saturday night and I was sitting home alone. My parents were out for the night. I was outside in the back yard, it was a warm night and I was only dressed gym shorts and a t shirt when I heard someone calling my name I looked up and it was the neighbor, "Hey if not busy come over and hang out for while have drink or something?" He was saying.

I went over and he asked me inside, we went into the kitchen and then he said to follow him down stairs. He took down to the basement where he had a game room with a built in bar, a nice a nice game room, pool table, pinball machine, very nice!!! A big leather couch and TV. I didn't know what he did for a job but he obviously made good money to have a setup like this. He told me to take a seat at the bar and then asked what I wanted to drink? I said, "Oh I don't care what ever you are going to have will be fine thanks."

He made us a couple of bourbon and Cokes and sat down beside me on a bar stool. We had a few drinks and talked, he asked me about school? And what I was going to do? He asked if I had a girlfriend? Then laughing asked if I had a boyfriend? By now the whiskey was working and I was getting a little loose. I told him no, no boyfriend or girlfriend just my hand. He laughed hard and said, "Yeah I understand, it's that way sometimes!!!"

We had a couple of more drinks and then out of nowhere he said, "So you jack off a lot huh!!"

By now I was loose and answered, "Yeah I jack off every day!!!"

He looked at me and asked,"You ever jack off with another guy?"

I was loose enough the question didn't bother me, I answered him truthfully and said, "No I haven't jacked off with anyone before just myself!!!"

He looked at me quietly for a few minutes like he was thinking about something then asked, "Do you want too?" "Do you want to find out what it's like to be with another guy?"

I was a little shocked by the question but I was half drunk and the question didn't offend me it made me curious? I said, "I don't know what you mean exactly?" "Do I want to jack off with you?" "Or find out what?"

He looked at me and stood up off of his bar stool. He unbuttoned his jeans and pulled his dick out saying, "Jack off for now then we'll see?"

The neighbor then started stroking his cock in front of me jacking off as I watched. He walked over to the couch and before sitting down took his jeans off leaving himself completely naked from the waist down, then he sat down saying, "Come over here by me I won't hurt you!!!"

As I got up off of the bar stool I was sitting on I could feel that my own cock was stiff and bulging out in my shorts. When I walked over in front of him he stopped me and turned me around so I was facing him he reached out and yanked my shorts down around my knees. My cock sprang out in front me, right in his face. He looked up at me and said, "Nice!!!" "You have a nice cock, I think I am going to have to have it!!!" "I think I am going to have to have you and your tight little butt!!!" "Why don't you take your clothes off and get naked!!!" "Then you can lay across my lap like a good boy!!!"

I slowly took my clothes off not sure what was going to happen. I didn't move I stood frozen, then I felt him taking a hold of my hand and guiding me down and across his lap placing my hard cock in between his bare legs. Then I could feel his hand on my butt massaging my cheeks, gently rubbing them, squeezing them firmly, spreading them apart. As I laid across his lap I could feel his cock poking me in my side and in my belly. I could feel myself trembling but I wasn't sure if it was from fear, or from excitement!!!

"What are you going to do to me?" I asked.

"What ever I want to!!!" The neighbor replied.

"You have a nice butt and I like young men's butts!!! "So I do know one thing, I am going to have yours tonight!!!" He nonchalantly replied.

"Now spread your legs for me like a good boy!!" He said in a matter of fact tone of voice.

I spread my legs, then I felt him reaching in between my thighs and cupping my balls, gently squeezing them as he rubbed his thumb up and down behind my balls, rubbing his thumb from my balls towards my asshole until he was almost touching my asshole. This made me utter a little moan of pleasure. "Good boy, feels good huh?" "Just relax I won't hurt you!!!" He said as he moved his thumb back and forth behind my balls

sliding it up close to my asshole.

"UH, HUH!!!" Was the only thing I could manage to say.

"Your a naughty boy!!!" "I think you need a good old fashioned spanking on that tight little ass!!!" He said in mischievous playful kind of way.

I could feel him removing his hand from between my legs and then without saying anything brought the palm of his hand down hard on my left butt cheek causing a loud squeal to escape from my throat and then he brought the palm of his hand down hard again on my right butt cheek causing another loud squeal to escape my throat, this time making me kick my legs out straight behind me causing me to squirm on his lap. He did this for what must have been a good ten to fifteen minutes smacking me on each cheek making me kick and struggle!!!! "Good boy!!!" "Good boy settle down, settle down now!!!" He said in calm soothing voice.

"OWWW!!!!" "OW!!!" "That hurts, that fucking hurts!!!" I was saying as he began rubbing my butt cheeks again, rubbing them and spreading them apart as he massaged them soothing the stinging, helping the burning sensation to slowly go away.

"Stand up now I want to watch you jack off, then I am going to put on your knees and your going to give me head, your going to learn to suck cock!!!" The neighbor said in a dominant matter of fact tone of voice.

I slowly crawled off his lap and stood up then I turned to face him and slowly started stroking my cock. "like this?" "Is this what you want?" "You want to watch me jack off like this?" "like when I am at home in my room and I do it!!!!" I teasingly asked him as I stood in front him stroking my hard cock in my hand, I was jacking myself off hard now as he watched me.

"Now you are going to make me suck your cock?" "I never done it before I don't know how?" I told him as I stood in front of him masterbating.

"Yes now stop that before you make yourself cum all over my floor!!!" "Come here, right here between my legs and get on your knees!!!" He ordered me as he sat on the couch slowly stroking his own cock up and down as he watched me jerking off.

I slowly lowered myself to my knees as I made eye contact with him. I placed my hands on his knees to steady myself as I knelt in between his legs and leaned in towards his crotch. I reached out and took a hold of his erect penis in my hand and guided it towards my mouth. It felt huge in my hand and I could see the big blue viens that ran up and down the length of his shaft, I could feel it pulsing in my hand as I slowly flicked my tongue across the head tasting his salty dried piss. I slowly lowered my head taking it in my mouth. As I began to cautiously suck on it I heard him groaning and felt him pushing his hips up towards me forcing himself deeper into my mouth.

"OHH YEAH JUST LIKE THAT!!!" I could faintly hearm him saying. As I began moving my mouth up and down on his shaft gently sucking on his cock. I felt his hands on my shoulders gently touching me affectionately letting me know he was liking what I was doing for him. I took my left hand and let wonder in between his legs and began gently experimenting, carefully playing with his balls squeezing them and rubbing my fingers in between his thighs and down by his butt crack.

"Easy, take it easy not so fast, we have a long way to go yet tonight!!!" He was saying trying to slow me down a little trying to make it last.

I pulled my mouth off of his erection then looked up at him for guidance, "Just slow down and take easy, don't make me cum not yet, I'm want your ass before we're done!!!" He said in slow calm voice letting me know what he wanted to do to me, that he planned on fucking me before he was through with me.

I lowered my head back down towards his crotch and continued to blow him. I was hearing myself making wet slurping noises, as I slobbered on his cock eagerly working my mouth on it. He let me suck him like this for another few minutes before stopping me, telling me,"Hey, hey wow good enough for now don't make me cum!!!"

I pulled my mouth off his cock and he helped too my feet telling me, "Take a seat for a minute and have some of this it will help you relax!!!"

As I sat down on the couch he handed me a joint telling me, "Take a couple of hits of this and mellow out, relax I'll be right back."

I took a few tokes, as he left the room for a couple of minutes. When he came back he mixed us each a drink and then came and sat down beside me offering me a drink. I took a sip of the drink and looked around to see what he had sat on the end table. When I looked on the table I saw there was a bath towel and a big jar of Vaseline. "What that's for?" I innocently asked.

He looked me directly in the eye and calmly said, "That is too grease your asshole, I'm going to fuck you, I'm going to fuck up your butthole!!!"

I looked at him not knowing what to say or do, I was stunned and speechless. I just sat there looking at him, staring at him before I finally managed to say, "Will it hurt?" "Will it hurt me?"

"I will go slow and take it easy on you!!!" "I will open your ass with my fingers first." "It might hurt a little bit at first, but I will be easy on you!!!" He said in a quiet calm voice that made feel better, he made feel like I could trust him.

"Finish your drink first that will help you relax and calm down!!!" He said as he let his hand find it's way to my thigh and eventually to my cock stroking me slowly as I finished my drink. The alcohol was giving me a warm feeling in my belly and I could feel myself calming down as the bourbon slowly made it's way into my blood stream.

"When you are ready I will put the towel down and then go ahead and kneel right here on the towel, then lean down and rest your head on the arm of the couch!" He told me as he patted the cushion I was sitting on.

I finished my drink and stood up. He laid the towel down and I crawled up on my knees and did as he said. When I rested my head on the arm cushion my ass was pointing up in the air towards him. I felt his hands on my butt massaging my cheeks gently spreading them open exposing my asshole too him. "You have a beautiful little asshole, I like the way it's pink and puckered up!" He whispered quietly.

I felt his warm breath on my cheeks and realized that he was very close to my ass, I heard him sniffing me, smelling my asshole. I couldn't believe that he was doing this, smelling me there, smelling my dirty asshole!!!! This aroused me terribly I felt my cock twitching and my balls tightening up and aching at the thought of what he was doing to me, smelling me there. My god I thought to myself how sick is this he is smelling my asshole smelling me where I poop from. I thought about how much I was loving this, the intimacy, the nastyness of him doing this to my ass.

I took a deep breath and felt my body relaxing. I felt safe and was enjoying what he was doing to me. It was extremely exciting and arousing to have someone doing these kind of sexual things to me, to my ass, my most intimate and private place. As I relaxed I felt the tension leaving my body, I could feel his mouth on my butt cheeks going from one check to the other check gently kissing them, gently sucking on them.

I felt his mouth on me just below my tail bone then his tongue trailing down my butt crack to my balls and then back up stopping where my asshole lay hidden between cheeks. I felt my cheeks being gently spread open and then his wet slimy tongue on my hole. Licking up across my asshole and back down towards my balls. Then slowly back up towards my butthole stopping directly on my opening. I moaned uncontrollably out loud, "OHHWW!!!!" "IT FEELS GOOD!!!"

He didn't stop too say anything he just spread me wider pushing his tongue into me, into my asshole!!! "OHH MY GOD WHAT ARE YOU DOING?" "IT'S MY ASS, MY GOD IT'S MY ASSHOLE!!!!" I heard myself saying loudly as I panicked at the thought of what he was doing to me.

I felt his tongue pull away then I heard,

"SHH, SHHHH!!!" "RELAX IT'S OKAY, I KNOW IT'S YOUR ASSHOLE!!!"

"I'M SORRY I HAVE NEVER HAD IT DONE TO ME!!!" "I CAN'T BELIEVE YOU ARE DOING THAT TO MY ASS ISN'T IT NASTY?" "DON'T I SMELL BAD?" I embarrassingly said trying to apologized.

"No your ass isn't nasty!!!" "And it doesn't smell bad, it smells like a dirty ass and it's turning me on!!!" "It's making me want it all the more!!!" He told me. Then with out saying anything more I felt his tongue back in between my ass cheeks delicately probing my hole testing me to see how I was going to handle it. After a few minutes of delicately tasting me preparing me for more. I could feel his slimy wet tongue slithering through my asshole and probing into my rectum tasting me on the inside.

"OHH IT FEELS GOOD, YOUR TONGUE FEELS GOOD INSIDE OF ME!!" I moaned.

He passionately ate my ass for a few more minutes, reaming deeply with his tongue working my hole, opening it up getting me ready for his cock making me feel good.

My mind was blown by the thought of someone doing this to my asshole. By someone sticking their tongue up my ass, sticking their tongue in me where I go to the bathroom from. I couldn't believe he was doing this to me but it was turning me on, the feelings of his tongue slithering in and around my asshole was driving me crazy with lust. I was ready to feel more in my ass.

I was ready, I was ready for him to take my ass, to butt fuck me!!! I was ready for more, I wanted to experience more of this dirty raunchy raw sex.

"PLEASE!!!" "Please I want it now!!!" "Please give it to me!!!" I heard myself saying, asking for more.

"Are you ready?" "Are you ready for me to take your cherry?" He asked after he let his tongue slide out of my asshole.

"Yes!!!" "Yeah I am ready for you!!!" I answered as I lowered my head back down on the arm of the couch and arched my back pushing my ass back towards his cock.

I felt his body, his chest sliding up over my back and his hand gently lifting and turning my head so I was face to face with him, "Do you want to taste your ass?" He coaxingly asked.

I just stared at him not saying anything as he took his hand and guided my mouth to his mouth forcing his tongue into my mouth letting me taste my own asshole, my own filth. Then he gently let go of my head and moved back behind me.

I could hear him moving around behind me when I heard the lid being taken off of the jar of Vaseline, "I'm going to grease your ass and open you up with my finger." "I want you to relax and talk to me, tell me what you are feeling!!" He was saying in a calm relaxing, soothing tone of voice, trying to keep me calm, preparing me for the loss of my virginity, the loss of my anal cherry.

"Ok I'll try, I'm really nervous!!!" "I want you in me but I'm scared!!!!" I told him as I knelt on the couch with my ass in the air shaking with fear and excitement, waiting to be taken up the ass the first time.

I felt his fingers slipping in between my butt cheeks, they felt greasy and slimy with the Vaseline on them. I could feel him sliding them up my crack smearing the Vaseline on my asshole, then stopping and resting his two fingers against my hole as he massaged my butthole with his fingers smearing the Vaseline on my opening greasing my ass. It felt good, his fingers felt warm and slippery against the skin of my asshole, I could feel my hole relaxing and loosing up.

He must of been able to feel me relaxing as he rubbed my butthole. He laid his other hand on my back, gently began massaging my back and my ass cheeks with one hand as he lubricated my anus with his other hand. Slowly, very gently I felt the tip of his finger entering my asshole smearing some of the Vaseline in me, starting to lube me on the inside getting my butt ready to be penetrated.

When I felt his finger entering me my asshole involuntarily tightened up and clenched. "RELAX IT'S JUST MY FINGER, FIRST ONE AND THEN TWO, YOU NEED TO BE OPENED UP BEFORE I PUT MY COCK IN YOU!!!!" He was saying this in a firm serious tone of voice instructing me on what I needed to do.

"I will try, I'm nervous, I've never had anything in my ass before, I want it but I'm scared!!!" I sincerely answered him.

"I will loosen you with my fingers and then I am going to fuck you!!!" "Once I am in your ass with my cock I won't pull it out until I am done!!!" "I'm going to fuck you bareback, I'm going to cum in your ass!!!" He said letting me know what he was going to do to me.

"Yes Sir!" "I understand!!" I replied.

"This is going to make you feel a lot of different things, it's going to hurt you at first and it is going to be difficult for you, it is going to make you feel full!!!" He said letting me know what to expect.

"I want you to talk to me while I am doing it to you!!!" "I want you to let me know what you are feeling!!!" "I've never had a virgin before, I want you to tell me what it feels like!!" He said, asking me to describe to him what I was feeling while I was loosing my cherry, what it feels like getting my ass broke in!!!

"I will try, I'm ready, I want you to fuck me, I want to you to take me!!!" I answered as my mind was racing with thoughts about how it was going to feel? And what it would make me do? I was worried it might make me cry, or have a accident, I had no idea what to expect? I was half drunk from the drinks and still pretty high from the weed. And yet there was a small part of me that was feeling a little apprehensive not really sure I was ready!!! I was also so feeling overwhelmed with raw lust and desire I didn't care what happened to me!!!

I knelt with with my head down on the arm of the couch as he slowly started to push his finger into me, very slowly and gently pushing it into my anus. My mind raced with thousands of thoughts about what was going to happen? "What if I'm dirty?" I asked in panicked nervous voice.

"It's okay, that is just part of ass sex, that's what makes it fun, now relax!!!!" He calmly replied as he continued to slowly slip his finger into me.

"If it starts to hurt you, bear down like you are trying to poop!!!" "It will help you to open your ass!!!" He soothingly said in a warm caring voice.

His finger in my butthole was feeling good. I could feel it going in me deeper then I felt him stop pushing, I didn't know why he had stopped I just felt his finger stop moving. I didn't say anything just waited enjoying the feeling of his finger in my hole, when all of a sudden he pushed fast with a quick little jab. I heard a squeal escape my throat and felt myself arching my back trying to get my ass away from his finger. I was taken by surprise and startled, it didn't really hurt but I could feel my ass resisting his invading finger as my asshole involuntarily squeezed down on it as it slipped into my rectum. "Relax, relax now I'm in you all the way!!!" "That was your sphincter that I just slipped my finger through, now you can relax!!!" He said to me in a nice soothing voice.