My First Gay Anal

My first full penetration gay sex experience was with my FORMER gym teacher the summer after graduation. I was 19 and legal...graduated so he was no longer my teacher. Unlike so many gym teachers he was actually fit with broad shoulders teeny waist and a decent look to him. What none of us knew, at least what I didn't know was that he was gay. The first month after graduation I was working odd jobs trying to make money while I worked on getting a real job and hopefully go to college.

One of the jobs I did get was mowing Mr. Peterson's lawn, my former gym teacher from 9th grade all the way through graduation. It was a huge lawn which took me a few hours to complete and which I had to mow at least once a week to keep on top of the rapidly growing grass. One hot Saturday I was asked to mow it early because it was going to be too hot to mow it in the afternoon, that and it was supposed to storm that afternoon. With the way his grass grew after a rain I'd have a hard time mowing it with my push mower so I got there at 8 a.m.

As usual he was nowhere to be seen except a glimpse of him walking through the house every so often. Being naïve at best or severely stupid at worst I had no clue about sex and the many confusing thoughts, ideas and desires I had been having since the age of sixteen.

Ray, my friend moved away in my senior year to Arizona leaving me to deal with my confused ideas about sex alone. I had a girlfriend but she was from a strict and religious family.

Around noon I had completed the front lawn of Mr. Peterson's house. As I was starting up the back lawn he came out with a glass of iced tea. We sat in the growing heat under the shade of one of the many huge trees he had in his yard. "How's your summer going?" he asked.

I responded with a shrug "Not sure...the only job I can get is mowing lawns. I mean it pays ok...but not enough to get a car." I had my eye on a truck down the street from my house, a Chevy S-10 but the owner wanted 5 grand and I was making maybe 50 bucks a lawn depending on the size of it.

"What kind of car are you looking at?" he asked smirking. I told him of the truck I had my eye on and what they wanted. He simply nodded and sipped his tea. Then Mr. Peterson said "You know Ray used to mow my lawn as well, right?" I nodded. That was no secret because Ray had told me that he had and arrangement with Mr. Peterson the year he left. It was Ray who suggested I ask Mr. Peterson for a job the day he left. In fact he insisted I do it right away.

"Yeah, Ray told me. It was Ray who suggested I ask you for a job." I said.

Mr. Peterson nodded. "Yes, he did tell me he would...I'm glad you didn't wait. This lawn is a pain to keep on top of.' He said. Then out of the blue he said 'Ray also told me about you two...and what you did together. He said you suck a mean dick."

I was sipping my tea when he said it and nearly choked inhaling a good bit of it before finally catching my breath. Mr. Peterson laughed gently stroking my back as I recovered. "You needn't be concerned...Ray used to talk to me about this stuff because he knew I was gay. He caught me with Jacob one day...we weren't as careful as we should have been and he walked in on us. I won't say what we were doing...but it was kind of obvious.

Anyway, Jacob and I split up almost six months ago when his job transferred him to Europe. Ray said that you were struggling with confusion of what you wanted...sexually. That you were still curious about...well...taking a cock anally...which he said he wasn't quite ready for when he left. He asked me to talk to you about it...and to see if I could help you in that department...if you wanted."

The fact that my cock was now rock hard gave me away, though I was nervous as you might imagine. "Um...I'm not sure what do say Mr. Peterson. Ray never said anything to me about you or what you did.' Then for some curious reason I blurted 'what were you doing when he caught you with Jacob er...your boyfriend?"

Mr. Peterson frowned...not seriously...hesitated then asked "Do you really want to know?"

I swallowed nervously...nodded 'yes'. He then leaned in put his hand on my shoulder...mostly to see if I would shrug off his touch...I didn't...then whispered into my ear "I was fucking him in the ass on our bed. Actually he was leaning against the bed and I was standing behind him...fucking him...hard. It was then Ray walked in on us. I was at the point where stopping was just not an option...and Ray watched me cum inside Jacob's ass...which is what Ray said you wanted to experience at some point."

I was feeling faint at this point both from the surge of desire, curiosity and from the fact my cock was sporting a raging hard on. Unconsciously I nodded 'yes' to his last sentence at which point I noticed the head of his cock protruding out of the leg of his shorts...he was also rock hard...and huge. His cock had to be 9" long...maybe longer. Ray had been 8" and kind of thick...Mr. Peterson...well he was 'thick' as well as long. Mr. Peterson smiled warmly stroking his cock through his shorts "Well, if that is the case then maybe I can help you' he said 'but you have to finished the lawn, I can't have you stop halfway through your job. However, as it is my back yard and I have a tall privacy fence built all the way around it...I want you to mow my lawn naked."

I stood up...dazed. My shirt was already off so when I stood my shorts were the only thing left on. Mr. Peterson then unbuttoned my shorts...and pulled them down. I stepped out of them...nervous...scared...but turned on like I had never been before, turned on by the knowledge that I was going to experience my first anal sex...with a real cock. "Turn around...Rick...turn around...let me see that fine ass of yours." When I did I felt his warm hands stroke my thighs...and work up to my ass...cupping each cheek...followed by a low grumble of emotion...which I took as his getting turned on. His cock was also raging...and hard to miss as he stood up and pressed it hard against my ass. He had pulled his shorts down and it was now free of their confines. I felt it prod my thigh and slide up my ass crack. It was then I knew what I wanted. Then with a swat on my ass he sent me to finish my job naked...and he watched from his chair as I finished his lawn with his cock twitching in the hot afternoon air.

An hour later Mr. Peterson walked me into his home and into the enclosed patio where he had a nice hot tub but that is not where we went first. He took me to the bathroom where he had a specially designed toilet and a hose...the details you don't need to know...but we spent the next 20 minutes taking care of my cleansing. "I never like fucking anyone unless we've prepped them for it. It is much more pleasant and sanitary" he said as he led me to the hot tub.

Once in he handed me a beer before crawling in with me. "Ok, nothing will happen that you won't enjoy...and that you won't want first. It may be that nothing happens today...but I have the impression that something might."

I hadn't said two words since I had started mowing his lawn naked but now I was shaking in apprehension and anticipation, my eyes locked onto the head of his cock protruding from the water...a good two inches of his fat cock was out of the water staring right at me. Unconsciously I moved my hand to it...and wrapped my hand around it. A groan of anticipation escaped Mr. Peterson's throat and mine. He stood up and let me have a look at his 10" fully erect cock, no pubic hair...nothing to get in the way of my feeling every last inch.

I looked up at him...as he sat back down. "Will it fit?" I asked

He stroked my cheek...and pulled my face to the end of his cock "If we take our time...yes' my mouth engulfed his head 'ohh..Rick...Ray said you could really suck a mean cock...lets find out." And we did. I had been sucking Ray off for well over a year and I'd actually let him cum in my throat. The first time it was more of a passionate 'what the hell' moment when he was fucking my mouth and grabbed my head shoved his cock deep and unloaded. I liked it and had taken his come many times since.

Mr. Petersons cock was thicker but not that much thicker than Ray it was certainly longer for sure. I had not deep throated Ray, I'd gotten close...but I'd not been able to get all of him. Mr Peterson had the patience of Job and let me take my time on him. My mouth fit over his cock nicely and I got a good bit of his shaft into my mouth without much hassle. He was sitting on the edge of the tub and I was inside standing in the water bubbles jetting around my body. It was the perfect angle for me to slowly get used to sucking his cock. His moans of approval spurred me on and I slowly took more and more of his cock into my hungry mouth.

As I got into my rhythm I felt his hand cup my neck and begin pulling me onto him nudging my mouth onto his cock fractions of an inch more each time. "Oh..my god...you are a natural. Ray said that you liked swallowing his cum...is that so?" I nodded not wanting to take his cock from my mouth. "Good...only I don't know if you can take my whole load. Are you willing to try?" he asked. Again I nodded. This time however, I looked up at him to emphasize that 'yes' please I would like to take his cum. We continued like this for a while because he had stamina and I had to occasionally stop to sip beer and take a breath and to make our time last longer. I was really enjoying myself and I wanted it to last a while.

In between our sessions we talked about how good I was doing and if I was sure I wanted to swallow and such. I said I wanted to and even hinted at wanting to deep throat which he seemed to like but agreed that it would likely not be that first day. I took his cock back into my mouth again and got quickly into my rhythm and he also quickly placed his hand in the nape of my neck and helped me along. He then began speaking softly to me "You know I always wondered if you were at least curious. Most young men are at some point...Ohh..yea...I'm getting close...soo close...this is your last chance to back out...otherwise I'm going to let you have it...all." My response was to increase the depth of my strokes so that I could feel his head hitting the back of my throat...not quite getting 'there' but close enough to matter when suddenly I felt his cock swell, his thighs twitch...and his hands close on my neck and pull my mouth onto him as he cried out "Oh...god...yes!!" and exploded in my throat. The head of his cock was pressing hard against my opening...as I felt hot jets of his cum shooting down my gullet. I held my breath and grasped his thighs from underneath to anchor myself onto him as I took his cum. He grunted again and shot another jet down my throat and the release his grip on my neck. I remained where I was because he was still shooting cum..and I didn't want to miss a drop.

Pulling from me he then slid into the water and handed me my beer, breathless as he looked hard at me in serious contemplation before saying "If you will allow me, I will help you learn how to deep throat a cock because you are excellent at it. I mean that.' he said as he pulled me to him in the tub and wrapped an arm around my waist. 'If you enjoyed that I think it is safe to say that you will love getting your ass fucked."

I was feeling pretty good about what we'd done up to that point and was thinking that I'd like to take this thing further if he wanted to, I certainly did. I sipped my beer and let myself fall into his shoulder letting the beer and water sooth me while at the same time my desire and nervousness grew. The conversation was his interrogation of what I had done so far and with what toys specifically dildos. I told him I'd used an old fashioned vibrator that was 7" long and not very thick, but it had been enough to let me know that I'd probably like the real thing in time.

As we talked and as the beer turned to wine Mr Petersons hand slid down my back and to my ass and was eventually positioned so that I was sitting on his hand with his middle finger probing my hole. Eventually he had worked it into me a good way and I was responding so that he knew that I did indeed like what he was doing. "You'll need some attention down there before we try the real thing." At first I thought that we weren't going to 'fuck' yet and I was so ready that my disappointment must have showed. "Oh, don't you worry love...you'll get my cock...today but we are going to have to get you ready for that first..besides I want to play with that sweet ass of yours first.' He moved it, kissed my neck the whispered 'you won't be disappointed...not by a long shot"

He finished his wine and poured me some more then asked me to lay face down on the platform at the edge of the tub so that my ass was just above the water. It was here I discovered that there were shelves that happened to fit my legs perfectly so that I didn't have to work too hard to keep myself in position.

In my ignorance I thought that maybe he was going to go right at it and take my ass right then...but I was pleasantly surprised by the fact that when he stepped behind me his face was right at my ass, more specifically his tongue was at my ass. Hot breath mixed with the heat of the water and the cool air over my wet body. He kissed each cheek gently one then the other and spread my cheeks and slowly licked my rosebud causing me to shudder and moan with pleasure "Ohhh.." is all I could say as my body shook with tremors of excited bliss and desire to learn so much more. One lick...one minor probing...another circular lick...more probing...mixed with a sucking noise followed by a wild mind numbing feeling of having his tongue drive into my hole.

Unconsciously I reached behind and pulled my cheeks apart as a clear signal that he could go deeper if he wanted to. It felt to me like a foot long snake had just burrowed into me. Another 'Ohhhhhhhhhhaahhhhohhh" came from the deepest reaches of my body as I gave in to his wisdom and experience. He chuckled pulling his tongue from me "if you like this babe...you are going to love my cock"

My answer was merely to reach behind my ass and pull my cheeks apart in a silent, urgent request for him to continue to which he again chuckled and proceeded to drive me insane.

I lost track of time as he clearly ravaged my hole with his eager, experienced tongue. I was breathless and so horny when he finished that I was at a loss for words. I hadn't spoken much since we'd begun but then there had been no need. When I sat back down into the tub I noticed that it was not even two in the afternoon. As I sat down his hand was once again 'there' this time with two probing fingers that were immediately driven into my waiting ass...to my delight.

That it was only two in the afternoon excited me because my parents had left the night before on a weekend trip with friends and wouldn't be back until the next afternoon. I had all day and maybe even all night to experience those delights I'd only imagined in the darkest hours. However, the tub was beginning to lose its warmth because something in Mr. Petersons heating element quit. So we got out and headed to the living room.

In his room was a playpen type sofa where the entrance was one corner and the rest was covered in blue velvet pillows to match the upholstery. It was huge and was large enough to allow us to lay head to toe with a foot to spare on each end of us. "Lay face down, I'm not done with your sweet ass yet." I did not hesitate and neither did he by the fact that he was already between my legs and tonguing me before I was even settled. The angle was better for him and for me as I could feel his tongue burrowing into me even further. His arms wrapped around my thighs as his face burrowed into my ass. He was clearly enjoying himself and I was in heaven as I wrapped my arms around a pillow and moaned my own blissful approval into it.

To describe how I felt no words are possible. I had always loved ass play...but it had been adolescent nonsense compared to what I was experiencing at that moment. There were no doubts no fears...just bliss and a beautifully long tongue sliding into and out of my ass. On occasion Mr. Peterson would bury the full length into me and wiggle it about in a circle and slowly remove it and then slowly burrow back in to me. "Oh My God!" was all I could say when he shoved it deep. He certainly knew what he was doing and I was grateful for it.

On one of his rests he would lean his clean shaved cheek against my ass so I could feel his hot breath on my asshole he said "I always had a thing for you. You seemed to know what you were about, that and my gaydar would go off, just a little when you were near me. You have no idea how insane watching your ass made me. Then Ray told me what you two had been doing and I knew I had to see for myself. I'm glad Ray sent you in my direction" he said finally.

I moaned out a low "I'm glad he did to. I had no idea this could be so nice."

Mr. Peterson chuckled "I'm glad to. As for the rest you haven't seen anything yet. Just wait until I fuck you in the ass. You will love it, I promise." With that he repositioned himself at my hole and continued loving my ass for the little while.

It was another half hour before his insatiable appetite was satisfied and he finally withdrew from my ass just as the first of the afternoon thunder storms were hitting.

The thunder outside was a perfect background for the storm inside. We sat together sipping wine as we got ourselves ready for the next round. As the rain poured down my mouth once again found his cock and began working it easily sucking the tip and licking the underside as we both got lost in the storm. When I came back up for breath he handed me another glass of wine and said "I think we need to get you ready for me" and had me lay down again face down.

As I got back into my position I saw out of the corner of my eye Mr. Peterson pull a tube of KY lube from the cushions. My heart leaped into my throat in excitement and fear at being faced with what I had wanted since I was sixteen. Granted I was only 18 at the time, two years was a very different time frame then...it was forever.

Anyway, I trusted Mr. Peterson enough to know that I wouldn't feel any pain or at least not very much. As I said before I had been using a solid plastic vibrator for at least a year and knew that I liked it enough to want to try the real thing. That reality was facing me as I realized my fantasy was to become reality. My heart was beating mightily in my chest which Mr. Peterson could feel as he rubbed his hand on my back as he slowly worked his hand down to my ass, parted my cheeks and began to apply lubricant. His fingers were magic as they gently massaged the lube around my opening. When my hole had relaxed to his touch a finger penetrated me and spread more lube inside. I moaned in response which caused Mr. Peterson to probe his finger a little deeper and began to move it around in circles. "I'm glad you like this' he said 'but we will be taking our time so that you get the full benefit of enjoyment out of this, Ok?"

My response was a moan and to spread my legs for him inviting him to do more. He chuckled and responded by inserting a second finger into me. I again responded with a low moan of approval which was answered with a slow insertion of both fingers to the knuckle. He rotated his fingers around and pumped them slowly in and out stretching my hole each time by pushing in just a little deeper eventually he added a third finger which again caused me to moan approval but this time I lifted my ass to his attention pushing myself onto his fingers to the knuckle. "Mr. Peterson!!' I moaned 'this feels so good"

Again he chuckled and kissed my cheek. "My name is Charles or Chuck if you like. I want you to use my name when we are together like this. I'm not your teacher anymore. Since I'm going to fuck you, we might as well be on a first name basis don't you think?" My response was automatic "Yes, Charles...please don't stop"