Taking the Plunge Ch. 02

"Oh my god. Your cock feels so good, Tom. Now fuck me like you mean it."

My dick did feel good buried in Paul's hot ass. I had never fucked a woman in the ass in this position before. It was so much more erotic than kneeling behind. I looked down at my pubic hair smashed against his crotch and his hard cock between us, leaking pre-cum onto his belly.

Looking at his face I could see the lust in his eyes. That was another advantage with this position. I lay on him and we kissed. I could feel his rock hard cock pressing into my belly when our lips met. I pressed my tongue into his mouth and we kissed passionately as I slowly stroked in and out of his ass.

I withdrew until I could feel his sphincter gripping my dick head and pushed back in all the way. We both moaned in unison as I filled his rectum. I slowly fucked him like that for a minute or two.

I raised up off him and supported myself on outstretched arms before stroking into him faster. Paul got looser. The looser he got the faster I fucked him until I heard him say, "Ooh, Tom, don't stop. Fuck me, buddy. Oh god you feel so good. Oh, I love it."

Between the feeling of my dick pounding his ass and his vocalizations, I reached my peak and tumbled over sooner than I wanted. Instead of burying my dick deep in his ass while my cum exploded from me I continued to fuck him hard as stream after stream flooded his bowels. It was one of the best orgasms I ever had. I was reeling from the sensations as wave after wave of pleasure rolled through me.

"Oh fuck yes, Tom. I love it. I am so close to cumming. Stroke my cock, buddy and get me off."

Instead of using my hand I pulled out of his ass and quickly bent to take him in my mouth. I wanted the taste of his cum and the feeling as it filled my mouth. I got my mouth around the head and used my hand to stroke the shaft rapidly several times; anticipating the eruption.

Paul raised his hips off the bed and stiffened as he came. It was wonderful feeling his hot cum blasting the roof of my mouth and tongue. I savored the taste as I swallowed most of his load. Paul was completely relaxed as I sucked the last bit of cum from his slowly deflating cock.

I slid up his body and kissed him. When his tongue entered my mouth I coated it with the small amount of his delicious cum I had saved. We moaned together as we shared it. I rolled off of Paul and lay beside him, exhausted. Paul said, " Tom, you really know how to make a guy feel good. How was it for you?"

I was amazed by how arousing it was to fuck Paul. I could tell he had enjoyed it too. I loved anal with Marge almost as much as vaginal sex, but fucking Paul had been fantastic. Seeing the pleasure and lust in his eyes had me contemplating letting him fuck me. "What the hell," I thought. " I have already done things I never even considered. I might as well go for the whole enchilada."

I took a deep breath and said, "Well, you are my first guy, but I've had no complaints from the women I've been with. I can tell you this. I really enjoyed it. After watching how much you liked it I have decided that I want to try. The only thing I am worried about is if I can take your fat cock."

"Holy fuck, Tom. That's great." I could hear the excitement in his voice. "You won't regret it I promise. I won't hurt you and I'll stop immediately if you ask. I also promise to make sure you are ready and relaxed enough to take me. I have fucked plenty of asses so I know exactly what to do to make sure you enjoy it too."

Paul's promises and confidence were encouraging. I decided to trust that he would keep his promises.

I knew Marge loved it when we did anal and after seeing how much Paul was into it just now, well. This was a big step and I was nervous about his size. I didn't know if I could take him without it hurting like hell, but I sure wanted to try.

Although I do like it a lot when Marge plays with my ass, her finger is the biggest thing that's ever been in me. Paul's cock was a hell of a lot bigger than Marge's finger. Throwing caution to the wind, I decided to take the plunge.

"Okay, but you will have to go slow and if I ask, you have to stop no matter what. I really don't know if I can take you, but I'll never know unless I try."

Paul got up then. "Okay, let me go clean up some. I'll be right back." He turned and disappeared into the bathroom.

I waited patiently for him to return. The porn was still playing on the TV, but could not hold my interest. Oh how things had changed for me in less than twenty four hours. Yesterday at this time I would have rejected the whole scenario out of hand. Now here I was having discovered that I loved to suck cock and anticipating taking one in my ass.

Paul was gone several minutes before he reappeared with a plastic bottle in each hand. He sat on the edge of the bed.

"Take this in the bathroom and give yourself an enema. It'll clean you out so things won't be so messy."

"I'm not sure what to do, Paul. I have never done that. Could you come in and help me?"

"Sure. Come on." Paul got up and headed back to the bathroom. I followed. Once there Paul told me to get on my hands and knees with my ass high in the air. I laid a towel on the floor and did as he said. I felt the nozzle of the enema bottle as he slipped it into my asshole. I felt the liquid as it rushed into me when he squeezed the bottle.

Before he left the room he said, "Now just stay there like that until you feel like you have to shit and can't control it. Then jump up and empty your bowels into the toilet. It'll only take a few minutes."

Within minutes the urge to take a dump was too strong to resist. I jumped up and barely made it over the bowl to evacuate my bowels. When I flushed Paul came in and wet a washcloth with hot water. He made sure my ass was clean as I bent over holding on to the vanity. The warmth of the cloth on my asshole was soothing.

Paul instructed me to stay right where I was. I felt his fingers on my asshole as he rubbed lotion on it. The lotion had a minty smell to it and it got warm as he rubbed it in. His finger slipped inside me to the first knuckle. I moaned from the sensation.

"Okay, let's go back in the other room so we can do this. I really am wanting to fuck your nice ass. I'm hoping you like it too so we can enjoy fucking each other the rest of the week."

I was nervous as I followed Paul back to the bed. The porno channel was still playing but it was just background noise at this point. I was anticipating this with trepidation, but I really wanted to find out what it was like to be fucked by Paul. I just hoped I could take him.

I lay on the bed on my back and Paul kissed me. Then he kissed down my body to my knees. Down one inner thigh and up the other to my crotch. He stroked my dick and sucked on my balls until I was squirming under him. He released my ball sack and ran his tongue across my perineum to my puckered anus. Although I had tongued several assholes, having mine tongued was another first for me. The sensation as he tongue fucked my asshole had waves of pleasure coursing through me.

Paul quit stroking my dick so he could open the bottle of lube he had brought from the bathroom. I felt the cool gel on my skin and smelled the mint as he slid his finger into my ass all the way this time. I moaned as the gel heated up while he slowly stroked in and out of my ass. It was feeling really good when I felt a second finger join the first. That was the most I had ever had in my ass.

I could feel my sphincter gripping his fingers. The new sensation increased my arousal and elicited a low moan. Before long my sphincter loosened it's grip. That's when I felt a third finger join the other two. My asshole felt stuffed full as Paul continued to finger my ass. Paul got up on his knees between my spread legs. This was it. Now we were going to find out if I could take his cock and more importantly, whether I liked it. I was beginning to understand how a woman felt as she waited for a man to penetrate her. Paul said, "Hold your legs up for me, Tom." I complied.

I watched as Paul applied the mint scented lube to his cock. Using his hand, he raked his cock head through my ass crack. When the head passed over my anus I shivered. Paul slid his cock up past my nut sack and slapped my cock with his. He grabbed both our cocks together and stroked them.

Then he held his hand still and humped his cock through his hand. The sensation of his cock sliding along the length of mine made me moan. He stroked his cock through my ass crack again. It tingled every time his dick head slid across my anus. I realized the tingling was from the lube Paul was using. It was a very pleasant sensation.

Paul stopped and spread more of the mint scented lube over his cock. Then I felt his cock head pressing against my asshole. My nerves got the best of me. I panicked and tensed up anticipating the pain his huge cock would inflict on me.

"Relax Tom. I promise to go slow. I need you to push like you are trying to take a crap. It'll help relax your sphincter and let me get in easier. I gotta warn you. There might be a brief flash of pain and a burning sensation when I first enter you. If that happens it will dissipate quickly. If it hurts too much I will stop and we don't have to go any further. It will be totally up to you."

I put my trust in Paul and believed what he was telling me. "Okay, I understand. I really want to try this so go ahead. I need to know what it's like. You've got me so hot right now. " I felt pressure as he pushed against my asshole again so I pushed like he said.

Suddenly his dick head popped through and he was inside me. There was a little flash of pain like he said there would be. The pain burned hot but it subsided almost before it even registered. Paul held still letting me get use to the feeling of him stretching my asshole.

"You okay? Want me to stop just say so." Before I could reply I felt him start rocking gently back and forth letting the head of his cock slide through my stretched sphincter. God, that felt good. "No, don't stop. I want to keep going. Just take it easy."

That was an incredible feeling, but it changed quickly when he slid in another inch or two. Oh god did I feel full. It didn't really hurt but it was pretty uncomfortable. It seemed he was stretching my asshole to it's limit. Paul pulled almost all the way out and slid back in no further than he had been. He started slowly stroking in and out of my ass at the same depth. After a few strokes like that I felt him slide in deeper. It wasn't uncomfortable anymore. In fact it was feeling pretty damn good. So good in fact that it surprised me when I felt his hips bump against my ass cheeks. I didn't even realize he was slipping more and more of his cock in me until it was all in.

Paul smiled down at me and said, "There. You've got the whole thing in you. How does that feel now?"

The pressure on my prostate was sending a weird sensation through my dick. I could feel the warmth of the lube in my rectum too. It felt good, but I definitely felt my asshole being stretched.

"Oh my god, Paul. I can't believe you got it all in me without me realizing it. I do feel stuffed full though. Other than that it feels really good. Your cock feels so hot."

"That stuffed feeling will pass shortly and the heat is from the lube. If you are ready, relax and I'll show you why I like it so much."

I let my legs go and put my feet on the bed. I was ready. "Okay, but be gentle."

Paul withdrew his cock until just the head was being squeezed by my sphincter. The feeling of his fat cock sliding through it was amazing. Before he came all the way out he slowly pushed all the way back into me, then repeated. The sensation was incredible as he stroked me with long slow movements. It only took a few strokes before I could feel my asshole loosen up around his cock. Paul started fucking me with just half his length while increasing the speed and force of his penetrations.

His cock was feeling really good. I could feel every inch of it as he stroked in and out of my ass. The fear of him causing me pain was gone and I was ready to feel the full measure of his cock. I raised my legs high and grabbed the backs of my knees opening myself completely for him. Paul slid his arms under my legs and they ended up resting on his shoulders.

He picked up his pace to the point of making slapping noises every time his hips hit my ass cheeks. He was fucking me hard and fast now. Burying his cock deep each time he pushed into me. I was grunting with every stroke as wave after wave of pleasure washed over me. I could have never imagined how good it felt to be fucked like this. I knew at that moment this would not be the last time I had his cock in my ass.

Paul stopped and pulled completely out of my ass and rammed several inches of his cock back in repeatedly. I moaned with pleasure from the sensations that produced. He was driving me wild doing that. The sensations his cock head created every time it pushed back into my asshole were fantastic. Now I knew why Marge moaned so loudly when I did that to her. Just as I thought I couldn't take it any more Paul fully impaled me and stopped moving.

"Oh my god, Paul. Oh fuck that felt so good. Please don't stop what you were doing. Come on and do that some more."

Instead of heeding me he withdrew completely and changed positions again. He stood up and stepped through my legs so he was straddling my body length wise. He grabbed my left leg and bent me almost double. He guided his cock to my gaping asshole and slid it in. There was no resistance this time and it felt wonderful. He flexed his knees causing his cock to slide in and out of my ass.

In this position my dick was just inches in front of my face. I heard him say, "Stroke your cock for me, Tom. I want to watch you give yourself a facial when you get off." I knew it wouldn't take much to make me cum I was so aroused. Cumming on my own face would be another first. I stroked my dick furiously as Paul ravaged my asshole.

It took less than a minute until I was cumming. I felt the cum rising from my balls and opened my mouth to try and catch it. I watched the first stream explode from my dick. What an incredible sight watching the white liquid explode directly at me. It hit me in my open mouth and some coated my nose. The next stream missed my mouth and landed on my cheek. The last couple of spurts spewed cum onto my chin. I had given myself the facial Paul wanted to see.

As I was cumming Paul groaned and rammed his cock deep into me. He held still as he moaned through his orgasm. I got a warm feeling in my bowels as I felt his cock throb in my ass. When he quit cumming but his orgasm hadn't stopped racking his body, he withdrew from my ass and let my legs down. He kneeled between them and reinserted his cock in my cum soaked asshole.

His cock felt amazing as it slid in me. He started fucking me again with very slow strokes. After several strokes Paul leaned down and used his tongue to clean the cum off my face before kissing me. I loved the taste of my cum in his mouth. Paul lay still on me as his cock went completely flaccid and slipped out of my ass.

He sighed deeply and said, "Oh fuck that was awesome watching you cum like that. Between that and your virgin asshole I had one hell of an orgasm. I thought my nuts were going to spurt out of my cock I came so hard. God I love fucking you, Tom. That was right up there with the best I ever had. How about you? You sure seemed to enjoy it?"

"Enjoy it? Oh my god. I am amazed how good that felt. It was one of the best feelings I have ever had. I definitely want to do that again. I can't thank you enough for turning me on to this side of my sexuality, Paul"

"You're welcome. This is going to be one hell of a good week don't you think?"

I grinned at him. "If the rest of the week is going to be anything like the last two nights it'll be one of the best weeks of my life."

"Well, prepare for the best week of your life. Go clean yourself up so we can get some sleep. Tomorrow is going to be a hard day."

After cleaning Paul's cum out of my ass and using a hot face cloth to wipe off the lube I returned to climb in bed with Paul. He had switched beds. The question must have been obvious on my face because Paul said, "There's a couple of wet spots on that one."

That solved the problem of the undisturbed bed. We would use one for sex and the other for sleeping. The ironic part was that I no longer cared what the maid thought.

The next morning I woke with my piss hard stuck between Paul's legs again. This time I knew right where I was and who I was cuddled up to. I thought about the night before and my dick twitched between his legs. I was really glad Paul had introduced me to receiving anal sex. Although, my ass was a little sore from the pounding he had given it.

I started humping my dick into the hollow between his legs just below his ass. Paul moaned. I reached around and squeezed his hard cock. God it felt big in my hand. Paul rolled over and kissed me. I kissed him back.

"Good morning. You better stop what you are doing or we will be late for work and you know that can't happen. Lets get up and shower before getting breakfast."

We took a shower together. It was so hard to maintain control and think about what we had to do instead of fucking Paul as he leaned against the shower wall. We finished our shower, got dressed and went down stairs for breakfast.

We worked hard every day and played hard every night. This was all new to me and I enjoyed fucking and sucking with Paul. I think it was the first time I ever was disappointed that a job was completed so soon. I really hated it that the week was over and our freedom to have sex was coming to an end.

Things would have to be different once we got back home. Well,we still had one more night and we were making the best of it..... to be continued....