My First Gay Anal

Autumn Surprise

My first threesome

After the first month of summer break Charles, for the sake of keeping up appearances had me visit him every other weekend to mow his lawn. The last thing he wanted was for my parents or his neighbors getting suspicious of my frequent visits. Even though I was of legal age the town we lived in was stuck in the 1950's and homosexual conduct was not acknowledged, those who practiced it were social outcasts and quietly run out of town. If a local teacher was caught having sex with a former student regardless of it being legal, hetero or gay the world would come crashing down on both the student and teacher. So we had to curb the urge and cool things down in order to keep it going.

August came and went and I hadn't seen Charles since the end of July because he had taken a vacation to Europe. It was his annual pre-start of school two week vacation to France. The second half of August was spent getting his class calendar ready for the next year. But I had kept up my visit schedule to mow his lawn to keep up appearances so that his lawn was at least neat when he got back.

The few chances we had to see each other in August didn't leave us any time to do 'anything'. September rolled around and my lawn mowing duties were diminishing because some of my clients liked their grass to grow taller before the autumn frosts. So I started to lose spending money what I'd saved was almost enough to buy the S10 I had my eye on. However, one day when I went to see my S10 it had been sold. To say that I was bummed was a massive understatement. I literally broke down in tears because it had been the perfect car for me and now I had to start my search all over again while I kept driving my dad's puke colored van.

That was a Saturday and I was scheduled to mow Charles lawn. I didn't know if he was going to be there or not. It had been nearly a month since we'd had any time to ourselves. Saturday was his busiest day usually because the staff at the school had to help stock the class rooms and gym lockers with gear and school equipment. So I had resolved to mow his lawn and go home.

I was about halfway done when Charles came out with a glass of iced tea. "Hey there' he said handing me my glass. 'Sorry I haven't been around, school stuff." He said looking at me.

I nodded and sipped my tea. "Yeah, I know." I was still bummed about losing the truck and it apparently showed.

"Everything ok?" he asked putting a hand on my shoulder. I told him that the truck had been sold and that it had bummed me out.

He smiled at me and pulled me closer and whispered "I think I know what will fix your mood. Shut down the mower and follow me." His arm wrapped around my shoulder and we walked back to his house. "I would have you finish my lawn naked but the neighbor to the south has been working his property line the last few weeks. So I think it would be wise to not have you do that for the time being. But that doesn't mean I can't see you naked in my house."

The walk back was slow and sensual as I anticipated what he had planned. We entered the house and practically ran to the bathroom where I was cleansed and showered. We didn't do anything in the shower because he had other plans but he wouldn't tell me what they were. What he did say was that I was to put on a robe and meet him in the living room. So I did what he asked and went to the living room. He wasn't there but he left a note. "Wait here".

It was a few minutes before I heard the door to his garage open and his voice call out to me "Ok, come over to the garage door, and then close your eyes. I've got a surprise for you." I did as I was told and stood with my eyes closed. Almost immediately I felt his hand on my wrist. I felt the cool air of the garage hit my legs and the cold floor on my bare feet. He lead me to a spot turned me to face whatever it was he wanted to show me. "Wait a minute,' he said and I heard him shuffle away. 'Ok, open your eyes" he said at last. My S10 was sitting in his garage with its tail gate open, a mattress stuffed in the bed and Charles, sitting on the open tail gate with his cock ready for action.

I was speechless. "You've been doing such a nice job taking care of my lawn...and me I wanted to show you my appreciation" he said.

I wasted no time showing him mine and I rushed him and hugged him. "Maybe we should break it in" I suggested.

He smiled and pulled my robe off my body. "I think that might be a good idea" he said scooting onto the mattress and laying down giving me access to his now fully engorged cock. I crawled between his legs and licked his shaft from the base to the tip and back down again savoring his warmth on my tongue. The sighs he let out were music to my ears as I kissed and licked his cock until I moved to take his head into my mouth. It had been little over a month since we'd last been together so it felt good to finally feel his head slide over my tongue. Charles sat up and got onto his knees so that I could get onto my hand and knees giving him a straight shot down my throat.

Grabbing my head with his hands I could somehow sense his urgency and his impatience to impale me. As it began to register I felt his cock slide deep, past my tongue and down my throat. I wouldn't call it savage because I was in my own way ready for it but it was the first time he had shoved his full length into my throat without any warning. Not that I was protesting. The directness of it, the heat of his need drove my want to please him. Still, he was gentle, having not slammed himself down my throat. Had he done so I'm sure I would have loved it.

His cock was now in my throat and I felt his heat and pulse running over my tongue and his head stretching my esophagus. His voice quaked...and quivered "Are...are you ok?' he asked 'can I do that again?" he continued. Being that I was unable to answer verbally, having a mouth and throat full of his cock, I simply pushed my face to the base of his cock and took another inch into my throat causing him to gasp "I'll take that as a yes" and he pulled out so that his cock was half way out...and again he shoved his length down my now expecting throat. Lifting a hand to his balls I squeezed them gently causing him to groan.

He then pulled out all the way, leaving his head inside my lips and then shoved the full length deep. I loved how his cock felt sliding into me like that all the way to where his pubic bone hit my lips. I was loving it and I started to pull off myself and then rock forward taking him whole myself. It wasn't long before he was fucking my mouth with a regular rhythm, but nothing that I would have called savage because I'm sure that if I came home with bruised lips my parents would want explanations. Explanations neither of us were prepared to give. I was not counting the times he pumped his cock into me, I just loved the sensation of his touch again.

But before long I felt his cock swell...and his grip firm up...and his pace quicken as he started to pant harder and faster...until he shoved his cock deep...and unloaded his cum into my throat. "Gaaahhawd" is all he said as the explosive release shot ropes of hot sticky cum down my throat. As usual his load was pretty heavy and was not nearly done before I needed to breathe so I got a serious blast of cum on my face as I pulled off. Wiping my face off I crawled up to Charles who was lying sprawled out in the back of my new truck smiling his satisfied smile.

I lay down next to him "Thank You" I said.

I got up onto his elbow and smiled down at me. "It is I who should thank you. Not even Jacob made me feel like you do. I'm grateful that you came to me" he said. In that moment our eyes met and he rolled in to kiss me. The power of the moment must have done something to him because he was hard in a few minutes and ready for more. But we didn't do much right away, as he just cradled me in his arms for a bit. I could tell he wanted to ask me something, because I had come to know him well enough to know such things.

"What is it?" I asked before he could bring himself to say anything.

"What?" he asked.

"Charles...I know you well enough to know you want to ask a question,' I wrapped my hand around his cock and stroked it gently. 'It's ok, you can ask me."

He hesitated a bit stroking my thigh and ass then said "I was wondering what kinds of things you'd like to try now that you are well acquainted with gay sex. I mean, I don't want to bore you with the same old, same old all the time. So, I was wondering...if...if you might be interested in...' he swallowed hard...'if you'd be interested in...well...um...getting fucked by another guy while I watched? Then later a three way with you in the middle." He had choked the last sentence out clearly nervous about my reaction.

I sat up and smiled at him. We'd been talking about stuff like this for a while and I found it exciting. I liked the idea of his watching me with another guy. I also liked the idea of being in the middle of a three way. There was something about being skewered as it were on two cocks that made my heart race with excitement. "So you are serious about watching me get fucked by another guy? You know I already agreed to that at some point, thing is it is up to you to make it happen. Only I don't want the guy to be some troll or an extra hairy beast type. As long as you are in the room and are ok with me taking another man's cock into my ass...I'm okay with it. Also the three way is ok as long as there is no pain involved...I'm not into S&M." I was firm about the last bit.

Charles was already aware of that and was himself not into such things. He would have to make sure the other guy was not either. I rolled onto my stomach so that his stroking could include my ass because I wanted him to get the message I wanted more. He smiled at me as he grazed a finger over my eager, waiting hole. A finger dipped into my ass and he smiled "Well, as it happens...' he paused I have a friend in town who has expressed in interest in you. He as seen you from a distance already and is eager to make your acquaintance. I have already told him that I want to watch him fuck you and if you were agreeable, a three-way." At this he shoved his middle finger deep into my ass knowing that I loved it when he did that and that I would be rendered a willing puppet by his attentions there.

A few minutes were spent in speechless teasing of my ass. When he moved in and whispered "My friend is taking a shower and will be meeting with him shortly. Hopefully you and he will hit it off. If not we don't have to do anything. Ok?" He finished the sentence by shoving two fingers deep into my ass then saying "I think you will like him. That and he is a bit heavy in the cock department...you might like that as well" he finished with a chuckle as I moaned my approval.

Turning my head to face him I said "So you are serious about this?"

He smiled at me and said "Yes, I want to keep things exciting for us, you. Like I said I don't want you getting bored with me" finishing the sentence with a flare of his fingers which tickled my prostate causing me to moan my approval.

We got our robes on and headed back into the house and Charles brought out his friend. Archer was tall, Swedish body builder and wearing a terry cloth robe like ours. Only his was tighter in the shoulders and forced open in the chest area. He reached out a hand and said "ello, I'm Archer, Pleased to meet your acquaintance." He spoke in fairly well articulated English with only a hint of Swedish accent.

Archer had grown up in the US but had moved back to Sweden to look after the family business, which was in freeze dried food with an off-shoot business in caviar. They were apparently doing well because he was driving a new Rolls and was in town buying a house which he was planning to pay for in cash once he found what he was looking for. Not only was he wealthy he wasn't bad to look at either. His hair was blonde shoulder length with green eyes and muscles in the right places.

We all sat around the table each of us wearing a robe and nothing else. It had the hallmarks of a badly made, badly directed porn movie where everyone is practically naked while making small talk about nothing before someone makes an off handed remark before everyone is fucking in a choreographed orgy.

It was a clear set up. Charles was just waiting for the right moment to suggest we all go to the hot tub and relax. Of course there would be wine to loosen things up. Charles showed great restraint by holding off a whole 30 minutes before sending me to the hot tub.

"Archer and I have a few things to talk about before we join you. Here, take this and wait for us. I'll bring another bottle with us when we come." He handed me a bottle of white wine and even poured me a glass, over filling it. The point was made, as I understood his intent to loosen me up for his impromptu threesome, in which I was the center piece.

I was insanely turned on by the fact that I was going to be used so thoroughly. I was nervous about just how large Archer was supposed to be. Charles was not slouch but he hinted at Archer being 'hung' and he did not think himself at all hung at a neat 10-inches. How big could a guy get?

Half of my bottle of wine was gone before Charles showed up in his robe. It dropped and he naked as usual stepped into the warm water and smiled one of his embarrassed, questioning smiles and said "Well, how to you like Archer?"

I nodded and said he was nice enough and that we seemed to like each other well enough. I then mentioned that he was good looking. Smiling his infectious grin he said "Good, because he really likes you. He got a phone call from Sweden and had to take it otherwise he'd be here with me. He'll be a few minutes more. One thing I want to tell you. He and I are good friends from way back and I've told him that you are a good guy and are working your way through school and stuff. I can say for sure that he wants your ass in the worst way. His cock is pretty heavy but I think you can handle it. Besides I want to watch you get fucked. I think it would be sexy."

At this opportunity I asked him what he meant by 'heavy'. "So you have made reference to his being heavy in the cock area, what do you mean exactly? Is he fatter, longer...terrifyingly huge?"

Sipping his wine he shook his head to say 'no', while he swallowed his wine down. "No, no, nothing like that he is about as big around as I am, which is big enough I think, but he is a bit longer like 12 or 13inches.' He smiled and continued 'I would love to see you take his cock while you look me in the eyes. I think that would be so fucking hot. It might be interesting if you could deep throat him as well." He moved in close and whispered "You aren't upset that I want to watch you like that are you?"

I looked at him and smiled "No, we have talked about it enough, I kind of find it exciting that you want to watch me.' Leaning in further I lay back against him in the water 'besides I think it would be kind of hot to suck you off while he fucked me.' I paused stroking his hardened cock 'As far as deep throating him we'll have to see about that, I've been doing you like that...I've not had anything longer than you before...so we'll have to see."

Charles smiled and groaned his lust "Ok, I guess that is fair enough. We'll take it slow and see where this goes. But you don't have a problem trying to take him anally?"

I was silent for a bit then said "As long as we take it easy and no rough stuff I'd like to see if I can take him that way, if you want me to." I stroked his erect cock as he moaned approval.

Leaning in he whispered into my ear "I want you to have fun. This is not only a fantasy for me I want it to be fun for you." He then kissed me gently.

Archer came through the door a few minutes later. He dropped his robe and climbed into the hot tub. He was devoid of all body hair, no pubic hair, no chest hair nothing. But that was nothing compared to the fact that what he had swinging between the legs. His cock, limp had to be easily 9 or 10 inches long...flaccid. His girth was similar to that of Charles when he was flaccid but the length, well, that was and eye opener.

Archer smiled and settled into the warm water. He didn't waste any time with small talk and said "Well, Rick, Charles has told me what he would like to happen between us. Are you okay with that? If it makes any difference I would love to have my cock buried to the hilt in your ass." That said the polite conversational pretext was gone. I had either to accept the situation and go with it or not.

Charles slid his hand down to my ass and slide one finger down my ass crack and without preamble, warning or anything shoved his finger into me to the knuckle. I responded by closing my eyes and gasping approval. I turned to look at him and he was smiling his mischievously and saying "I think you should at least suck his cock while I play with you back here' emphasizing the statement with an additional finger which he shoved in deep 'that and I think we need to get you ready to take his cock in your ass."

The fact that he put his thoughts to words, clarifying that he did indeed want to see me get fucked by Archer helped me to relax and let things happen. When I opened my eyes I could see the end of Archers cock protruding from the water a good six inches. His girth was roughly the same as Charles but the length was nuts. I was amazed. He had to be 14 inches long if he was an inch.

On the urging of Charles who was now pushing me toward Archer so that he could pay more close attention to my ass, which I was loving. As I approached him I discovered that there was a small turn-style table now sitting under the water. I had not seen it because of the bubbles but now I could feel it. Laying on it brought my ass out of the water just enough to let Charles have access to my ass. It also placed me in a perfect position to take Archer into my mouth, at least the portion that was above the water.

Looking up at Archer no words were spoken, none were necessary and he slid his mouth over the protruding head of his cock. Archer gasped as the first six inches of his long cock slid into my mouth. As that happened Charles took up station behind me and proceeded to ravage his ass with his tongue. Taking a breath I slid up on Archers cock and then proceeded to take his cock deeper and putting his head under water the process. To do this properly he would have to come above the water every so often, take a breath and then proceed on.

Archer was amazed that this was happening. He was even more pleased to find that this young man was well talented in the art of cock sucking. Moving so that he was slightly higher in the water he pushed his cock down to an angle more suited to letting Rick exercise his talents further. In response to this Rick slid his mouth over the exposed cock again and then took him down his throat as his head disappeared under the surface of the warm, turbulent water. "Oh my sweet Lord" moaned Archer. Looking at Charles Archer asked "Does he swallow?"

Charles sat back stroking my ass and thigh as he sipped his wine and nodded "Yes, and he loves the feel of hot cum shooting in his ass to. So when the time comes you can take him bareback."

That they were having this conversation about me with me sucking his friend off did something to me that drove me wild. Sliding my mouth down even further onto Archer I felt the tip of his cock reach the point where the next thrust would see his head in my throat. It was here that I began to realize that I had only half of his cock in my mouth. How far down my throat could I take him? I wondered. I had not quite taken 8" down my throat and we had a good deal to go. Charles was 10" long and I had him down my throat regularly.