If You Drop Your Wallet in P'town

I was about 23 and only out of college a couple of years. I was working for a hotel and restaurant supply company spending half of my time at the home office in Boston and the rest on the road.

I had grown up in a small town in central Maine and going to school in Cambridge Mass was a real eye opener on many levels. The most exciting was my exposure to sex and drugs. Women were more comfortable with their sexuality in the city and there were drugs of all kinds easily found. I had a few experiences with pot and sex at home but things moved much faster in the Boston area.

People of both sexes were more open about their sexuality and I was meeting openly gay, lesbian and bisexual people. If I had previously met anyone that wasn't straight I did not know it living in Maine.

School was a continuous party occasionally interrupted by cram sessions before mids and finals. Somehow I got through with a good enough GPA and letters of recommendations from some helpful professors to land a nice entry level job in the Hotel Management industry. It was interesting and mixed with the travel I was living well.

When my boss approached me about an upcoming trip to Provincetown a couple of the guys snickered and made jokes that I really didn't understand and when I asked them what was so funny they just said if I dropped my wallet in a bar to kick it back to Boston before I picked it up.

I drove to Ptown enjoying the Spring weather and found where I was to stay and started sales calls.

I met a lot of nice people but was starting to think there were a lot of flamboyant ones around.

At the end of the day I found myself dying for a cold one and sought out a bar.

It was easily found as there were so many around. I stepped to the bar and ordered a cold one and taking the first sip looked around to see what the female partons looked like. There was quite a mix of the local population. I had found myself in a gay bar or one that supported a very colorful group.

I really didn't care and quickly finished my beer and asked for another. The bar tender seemed surprised to see me stay for another drink. Settling in and looking around more closely I made eye contact with quite a few men and women, all seemed friendly. I felt someone come up beside me and I turned to find a good looking guy about a few years older than me standing there smiling.

He said: "You look a little lost, here on business or pleasure?" The word pleasure seemed to slide off his tongue with some implied reference.

"I'm here for a few days on business. Are you a local yourself?" I asked.

He was dressed much as I was suit and tie loosened after the day's work.

He said that he was also on a sales trip for a wholesale food seller. We talked about the places we had visited during the day and found we must have missed each other on more than one occasion during the day.

As the evening moved on he and I were pushed closer together as the bar filled up and things were getting pretty wild. He was drinking rum and cokes and we were throwing them down pretty good when he leaned close to speak to me and coolly placed his hand on the top of my thigh. The side of one of his fingers came into contact with my cock. I was shocked but excited beyond my imagination. I had been having some interesting fantasies about opening up my sexuality and here I was a long way from home with another man's finger touching my cock. I guess that is why I didn't move as he touched me.

My cock was rapidly getting hard when he asked: "Is this new for you? Do you want to do this?"

When I paused before answering he moved his hand to cup my cock and balls squeezing them. I was getting too hard to deny anything else and said to him: "This is new for me but I am not opposed to the idea of trying something new."

"Well let's get out of here before you change your mind. I am dying to see this thing I am holding here." He said stroking my now full hard on. I was a little afraid to have to walk out of the bar with the front of my pants tented out but there was so much groping and kissing going on around us that hardly anyone noticed. Hardly anyone except the guy at the door and he must have been watching it all and was smiling as we stumbled out the door.

The guy at the door said: "Don't do anything I wouldn't do, but I'll do anything!" I got the feeling he was looking for an invite to join us.

My new friends name was James and he asked how close I was staying. I told him across town and he said: "Too far, I am just up the street. Lets' go to my place."

We stumbled down the street with his arm over my shoulder and mine around his waist. It was Friday night and the streets were wild enough that we went un-noticed.

We were at his place and made it too his room and fell through the door as he unlocked it. Once inside he pushed me up against the door and opened my fly to push his hand inside grabbing my now soft prick as he pulled my face to his and kissed me on the mouth surprising me. He must have known he was moving way too fast for a newbie like myself and breaking the kiss said: "Sorry dude, you have me so hot; I forgot this was your first time. It is your first time with another guy isn't it?"

I told him: "You will be my first."

Pushing he said: "First what, say it out loud, I want to hear you say it!"

With my cock rapidly getting hard I reached between his legs to cup his junk to find he was very hard and big. Very big. I am a good seven inches but he had me by inches and his cock felt like stone, a burning hot shaft of stone. I squeezed him and stroked him like he had done to me in the bar. I reached under his cock to grip his balls and it was like grabbing a couple of plums. They were as hard as his cock and as I held them said: "Yours will be the first cock I suck and I want to suck it until you empty your nuts down my throat. And I bet once will not be enough if this is as much fun as I think it will be."

By now he had my stiff cock and balls out of my pants and was stroking me as I was fondling him.

"Let's do this right; I could do with a shower how about you?" He asked me, slowing down our mad groping.

I didn't have to speak as he leads me by the cock to the shower. We quickly stripped each other down to the skin. He was about my size and in great shape. His now hard cock was bobbing around in front of his crotch like a weapon. I was surprised to see that he was completely shaved. I had only seen this in porn but realized I had never seen another guy's cock this close let alone hard. Another pleasant surprise is that he is uncut and his awesome foreskin covers his cock head. As I am cut the few fantasies I am having about cock are about uncut ones.

As we got under the spray I was happy to see that he had a premium room with a nice big shower with multiple heads. When I was wet he turned me to the wall and covered my back with some soft soap. As he worked the soap to a lather with both hands I leaned forward to lean on the wall spreading my legs silently inviting him to continue down between them. He didn't disappoint as he ran the side of one hand down between my ass cheeks and the other over my ass. He was massaging my ass with both hands and running them between my cheeks. He reached between my legs to grab my sack and squeeze it. He then reached around to find my cock and commented as he stroked it that he wanted to make sure I didn't go soft on him.

I told him I doubted that I would "go soft" for a while.

He replied: "Well some guys go soft when you play with their ass. Has anyone else touched you like this?"

"Not until now and I like it. I hate to admit it but I have kind of explored myself there tho..." I admitted.

"You should not be embarrassed by anything as healthy as sex. You would be surprised if I told you the things my wife and I do." He told me.

"You're married?" I asked surprised.

"Yeah and we are both bi and have an open and loving relationship. She knows that I love her and would never leave her but sometimes I just crave cock. She has her pussy raids as she calls them and we even have talked about bringing one of our outside partners to bed with us."

He now turns me around to do my front and it seems like forever before he has washed everything but my cock. As he soaps my cock it is just a hand job with lather. And I am afraid that I will cum and stop him saying: "Let me catch my breath before I cum, I want the first time to be on a bed."

"I bet you can cum right now and be ready for more by the time we get to the sheets." He says still stroking me.

I reluctantly pull from his grasp and turn him around to give him the same treatment he gave me. I am enjoying washing his ass. His entire body for that matter. Where a woman's body is soft and curved he is hard and chiseled. I am getting into his ass crack enjoying running my fingers down to his balls. As I run my fingers down between his cheeks he pushes back and when my fingers travel over his ass hole he opens himself up so that the tips of a couple slide into him. He groans and strokes his cock saying that he loves ass play and hopes I will like it as much as he does. I take the shower head down and put it on pulse and direct it right on his ass hole.

His moaning reaches a new level as I direct the spray on his hole.

Wanting my first cock in my mouth and right now, I hang the shower head back up and turning him around replace his hand with mine on his cock.

I ask him: "Wouldn't you rather have this fat cock in my virgin mouth than one of our hands?"

He quickly shuts off the water and throws me a towel and we dry each other off. Dropping the towels we stumble to the bed still pretty wet. He pushes me down and spreads my legs and kneeling between them takes my cock down his throat to the balls. I am amazed but grateful for his experience giving him the ability to pleasure me so. He sucks me so that I feel he will pull my nuts down my cock. Releasing me he pulls back, still sucking me, but now working his tongue on the underside of my cock.

Stroking my shaft he runs his tongue around the crown driving me nuts with pleasure. This guy is perfect for my first time. He knows what he is doing and I bet is willing to let me try anything I want.

Once again I am almost cumming and pulling him away from my pulsating cock tell him: "Wait, I am afraid that if I cum first I might chicken out and not suck you off. Let me suck you now."

"Something tells me that nothing is going to change this for you, but a during mans' first time he should have some control on the direction. But know that I want to suck you just as bad." He reluctantly tells me.

As we shift around so that I am between his legs I take his fat cock in my hand and just look at it. It is a thing of beauty. Long, hard, with a foreskin that covers the crown except just his opening showing. It feels hot in my hand and I automatically stroke him. I stroke the shaft and run my hand down to grab his ball sack and after rolling them in my hand, I move back to put pressure on his taint as I take his cock into my mouth. I am overwhelmed by the sheer pleasure of this act. I can only compare it to the first time I stuck my tongue in a young girl's pussy. This time it is on a king sized bed and not the back seat of my dad's car!

I can only get about a third of his fine cock in my mouth and suck him like I enjoy having mine sucked. I run my tongue around the crown and over the shaft. I pull back some and as I push forward taking a little more cock into my mouth I run my other hand down to his ass hole to run my fingers around it.

He lifts his ass up to give me better access to it. I am quite pleased with myself to be giving this guy so much pleasure the first time I suck cock. He has no shame as he uses his own hands to spread his ass cheeks open for more of my play.

"Oh fuck, push a couple of those fingers in me. I can't believe you have never done this before. Where did you learn this shit?" He cries out.

"I am doing just what I like or have wanted to have done to me. Enjoy because I am loving this." I tell him between sucks on his manhood.

"Well if you keep this up I am going to fill your mouth with my cum. Are you ready for that?" He asks.

I don't even answer as I speed up my sucking and stroking of his cock as I have two fingers deep in his ass working them in and out and over his prostate.

He pushes his ass even higher as he holds my head down on his cock and he starts to cum. The first two shots are a surprise and I am shocked by their intensity as his cock throbs and shoots its juice down my throat.

Wanting to taste it I pull back so that I am holding only the crown tightly with my lips and run my tongue around it. A shot and another fills my mouth giving me the first taste of another mans' cum. I have tasted mine from a variety of places but this is new and different. Nothing really unusual but I am enjoying the idea of bringing him off like this.

All too quickly he wiggles free from my mouth and hands and laying on his side says: "Come up here while I catch my breath."

As I lay next to him on my side he brings our faces together and kisses me forcing his tongue into my mouth searching for any remnant of his load.

His softening wet cock lays across my hard one making me shiver. He reaches between us and holding them together strokes us. The feel of his hand and his cock on mine is intense and I am again afraid I will cum. Working his cock head to press against mine he takes his foreskin and pulls it over mine. Words cannot describe the feeling of having his skin cover my cock head and I can only moan into his mouth trying to swallow his tongue.

"Lie back and I will suck you off before you shoot all over me." He says.

"Would you rather I cum in you than over you?" I ask as he turns to face my cock.

"Bro, I am fine with you cumming anywhere you want, but how about down my throat this time?" He asks.

As he is almost in a perfect 69 position, I maneuver his hips so that he has to cover my face with them. This hangs his cock over my mouth and I grab his ass with both hands and direct it into my mouth. I love the way it feels. He hasn't lost much in size, but he is softer and as I suck him I love the way his cock feels all spongy and yet solid in my mouth. This brings a moan from him but he keeps my hard cock in his mouth sucking and bobbing his head up and down.

He is caressing my balls and pushes one of my legs back and up to my chest exposing my ass for his free hand. Holding my leg in his arm pit I feel him run a couple of fingers in his mouth and caressing my cock with them he works up a lot of spit to cover them. He takes the wet fingers and places them right on my ass hole. He runs them around my anus and pushes a little pressure on it.

As exciting as this is I have a hard time relaxing enough to let him penetrate my ass. But I moan letting him know that I am enjoying it. I can only moan as his cock is returning to its' earlier tumescence filling mouth with hot man meat.

We are in a world all of our own making. I am sucking cock again after doing so just moments ago while its' owner is sucking mine and fingering my ass hole. The room is filled with the sound of our grunting and moaning. I have heard a lot of the sound of sex, mine and even others but this is like nothing else. There is no soft whimpering here just man sounds.

I don't know how long we sucked, stroked and fingered each other but it probably wasn't long as horney as I was. I came first shooting again and again into James mouth. He was working my cock over pretty good as he pressed his two finger tips into my ass hole, He was fondling my balls with his free hand. He was like a one man band playing in my crotch.

As I finished cumming he let my cock slip through his lips. He still was holding my nut sack and fingering my anus. He scooted forward to suck each of my balls in turn. As he had two fingers in my ass he moved down farther so that he could lick my ass hole. I had done this to a couple of women and only one really let go and enjoyed it. I think the others were too embarrassed to show how much they liked it. I had no shame about then, after sucking a near strangers cock and swallowing his cum and when he wanted to eat my ass out I moaned: "Oh fuck, I love that, eat my ass."

James must have loved it because his cock was back to rock hard and due to him having to move to eat my ass I could only get a couple of inches in my mouth but I sucked and licked him for all I was worth.

He had maneuvered both my legs up and under his arms to spread my cheeks with his hands and was acting like he was trying to devour my ass.

He asked: "I would love to fuck this nice tight little ass of yours, are you up for that?"

"If you keep eating my ass like that, there is no telling what I might do!" I told him, meaning it. I was out of my head as he was eating my ass hole. As much as I was loving it I was surprised that my cock was shrinking, but I really didn't care because it was all about my ass now. I felt so nasty with my legs in the air spread wide and James eating my ass that when he asked if I was ready for my first fuck I didn't hesitate.

He got up and went to his suitcase and got a bottle of lube and some condoms.

"It is more fun bareback but easier to clean up with a condom." He said.

I was looking at how big his cock was, all hot, red headed and bouncing around and was starting to have second thoughts about my ability to take him comfortably and told him so.

"Don't worry, I want you to love this as much as I do, so will take my time and we'll use plenty of lube. He grabbed a towel and placed it under my ass and started to finger my hot hole with a couple of lubed fingers. One went in quickly and before I knew it he was working me over pretty good with two. He then asked if I was ready to try three. He said if I was comfortable with three his cock would fit fine. I was hot enough and had enough liquor in my to be as relaxed as I ever would and told him to go ahead but go easy. I asked him what was the best position for me and he said he wanted me on my back as I was, so he could watch the pleasure on my face.

He. slid his fingers from my ass hole and quickly pushed his cock head to it before it could close. My anus closed around part of his cock head as I shivered with excitement. Not waiting for me to change my mind he pushed the entire head of his cock into me and my ass gripped him.

I couldn't believe how hot this felt and panting told him so.

"Holly fuck I cannot believe this, hold your fat cock right there and let me enjoy the first time I feel a cock in my ass."

I looked at my now shrunk cock and James seeing this said: "Don't worry it a minute you will have two cocks. Some guys go soft when getting fucked. I bet after a few more times you will be rock hard as soon as you feel a cock touch your ass hole." He tells me.

He asks if I am ready for more cock and I nod and ask for it slowly. He does just that as he pushes about two inches of cock into me. He is way too big for my first cock but we are committed now and I try to relax for it.

He pushes another couple of inches into me and I feel I cannot take any more and ask him to wait again while my ass hole adjusts to his size. He is a patient and understanding lover and reaches to caress my balls flexing his cock in my ass. This brings the desired effect and I ask him to fuck me.

Putting my ankles up by his ears he leans forward and kisses me slowly but firmly pushing his tongue into my mouth. I reach for it with mine and we tongue fuck each other. As he pulls his cock slowly out of my ass he does the same with his tongue. When he has just the head of his cock in me he pauses, flexes his manhood and slowly pushes his cock and tongue back into me. When he reaches his previous depth I reach back and spread my cheeks offering him more of my ass.