Category: Anal Stories

A First Time for Anal Play Ch. 2

by BigMan©

After my first experience with anal sex, I was hooked. The woman was quite a bit older, and I saw her for many years after the first time. We met occasionally, and she always had me masturbate for her, fuck her, and then sodomize her. I learned a lot, and even though I am sure she had other lovers, I know I was her favorite dick.

I also had other experiences with girls, but never found one who would take my thickness up her ass. Since I could now make love instead of just fuck to get myself off, I found girls more willing to try things if they were satisfied. I finally got to stick my fingers in this one girl's butt and she loved it. Came hard that way. I found a vibrator she had once, and we had some fun with it. Ruth was the preachers daughter, and I think she thought she had something to prove. She would give me head anywhere, and do almost anything I asked.

After we had been bed partners for awhile, she asked me why I was always trying to stick my finger in her butt. I told her it excited me, and if she let me teach her, she could have a pretty good cum from it. We experimented, and I got some lube and worked my finger in her anus for awhile until she didn't think it was so bad. I had her get on her hands and knees and I fucked her pussy senseless with my big rod. After her first cum, I continued fucking her, and this time, I reinserted my finger in her butt. Now that she had gotten over the fear of it, and knew it was kinda pleasurable, it heightened her feelings, to have something in both holes. It was also kinda cool for me to feel my finger on my own dick when it was in her ass.

I tried to put two fingers in, but she didn't like that. So I stuck with one for a bit, but then I got the vibrator she had, lubed it up and put it against her butthole. I turned it on and she went wild. I pushed it in a little and she began to cum immediately. I still hadn't blasted yet, so I kept fucking into her, and the extra buzzing in her ass was right on my dick, and after a few strokes, I came gallons inside her sweet pussy.

Another time, I fucked her with the dildo only deep in her ass, making her lie on her back holding her legs over her head. I varied the vibrator speed, and she loved it. I could tell she was ready to cum, and I plunged the vibrator in to the hilt, cranked it up and leaned down to suck her clit in my mouth. She popped good. Cum trickled out of her pussy, wetting my chin, as I moved the vibrator in and around her ass. She kept cumming and cumming, and I let go of her clit, rammed my dick in her sopping slit and fucked her till I blasted my nuts inside her. She loved assplay from that day.

Naturally, I wanted my dick in her virgin rectum, so after fucking her one day, and using the vibrator up her shitchute, it was time to plunder her butt with my rod. I took the vibrator out and pressed my dick head at her butthole and pushed. I got the head in and she began wailing. I told her to just relax, and in less than a minute, it would feel good. She kept hollering for me to take it out, but I was determined she would like it. I pushed in further, and began to fuck about 3 inches into her over and over. She was fighting me now and finally wrenched free, my dick popping out of her ass.

She got up crying and yelling at me and finally I got dressed and left. I know if she had just calmed down a bit, she would have liked it. As it was, she refused to see me again, and soon all her friends knew I was perverted, and all my fuck holes pretty much dried up. I was pissed. I found new holes to plunder, but I realized I really didn't enjoy girls. I wanted a woman. Well I heard that women liked younger men, but how to get one. Most the older women I knew looked at me like I was just a jerk kid.

During that time, a friend of mine who was gay approached me. He said he had heard I love butt-fucking, and he was available. I declined. I love women, and just couldn't see going that way. Well we stayed on talking terms and one day the inevitable happened. I was online, downloading and whanking off to some porn videos when there was a knock at my door. It was the gay guy. Brad and another friend of mine, Matt. They wandered over to the computer to see what I was doing, and we got into surfing the net awhile.

Matt left and I was stuck with Brad, the gay guy. Now we had been friends for years, and other than the one time he broached the subject, I had never been uncomfortable with him. Now for some reason I was distinctly uncomfortable, tho. We continued surfing for awhile, and I got uneasy and quit. We were sitting there, and he said.

"You're hard, and I can take care of that. You don't have to touch me, just let me take care of that dick for you."

Well against better sense, I needed to get off, and here was an offer, so I unzipped my fly and hauled my pole out. He looked at it appraisingly and asked if I had ever been deep-throated. I told him no, no one had ever been able to get it all the way down. He pushed his chair away and knelt between my legs and grasped my pole. I leaned back and closed my eyes. His mouth closed over the head of my dick, and he swirled his tongue around poking at my pee-hole. He let go and licked the under side of my shaft and then down to my balls. He undid my button on my pants and pulled them down. Now he took my balls and began to mouth them, rolling them around. His hand was slowly wanking my shaft as he gave me a pretty good ball job. Then my dick was back in his mouth. He went down on me taking more in each time. My dick was at his throat, then in his throat and then down his throat. He would suck about half up and down and then slide a much as he could in and hold it and the start again. Finally I felt his chin on my balls. I looked down, and his face was red and straining, but all of my pole was down his throat. I could feel him gagging slightly and it felt unbelievable around my dick. He pulled off and eventually after more of the same, he swallowed everything I shot at him down his throat.

Well this was awkward. I looked down at my deflating manhood, he had some of my cum dribbling out of his mouth, and his dick was in his hands. He stood up, his dick hard and jutting out of his shorts, and went to the kitchen. He came back with some paper towels and handed them to me. I wiped up my dick and tucked it back in my pants.

We talked a few, and he asked how I liked it, and would I be willing to let him suck me off again. I admitted I would, and he just grinned. Then he asked if I would fuck his ass. I really wasn't sure and told him I had just let him blow me cause I needed relief. He challenged me that if he could get me hard, then would I fuck him. Well I didn't really think I would get hard with him, but I agreed. I stood up and stepped out of my pants, and sat back down. He took his pants off too, still hard and knelt in front to me.

He did pretty much the same as before, sucking my balls and licking and sucking my dick and finally deep-throating me. I got hard. He asked me how I wanted to fuck him. I just looked confused and he said do you want me on my back or on my hands and knees. Hands and knees I told him. He went in the kitchen and returned with some vegetable oil. He pulled out a condom, rolled it on, coated my dick with the oil, and then went over to the couch and leaned over it, his ass in the air. Well, my dick took over. He was shaved smooth, but his legs were still hairy and his balls were hanging there, so it gave me pause. But here was an ass. I hadn't fucked one in awhile, and I realized I wanted to feel the tightness and heat that only and ass has, so I lined up, grabbed my pole and pushed at his brown hole. It was great. That feeling of my mushroom head being squeezed as I pushed thru his sphincter.

I shoved in hard, once my head was in. I sunk about halfway in. I felt him tighten for a sec, but then relax. I began to fuck his ass. Just a good steady rhythm, back and forth. Soon I as balls deep, and it was a funny sensation to feel my balls swing forward and slap his.

I picked up the pace, and as my nuts drew up, I was enjoying the feel of moving back and forth fucking into a tight ass. I knew I didn't have to hold back, this ass could take it, so I began fucking into that shit chute really hard. Brad asked me between gasps if I had ever stove-piped. I asked him what he meant. He said to take my dick out. I did, feeling the pull as I popped out. His asshole was still wide open. He said to put it back in and then pull it out. Man that felt good. Feeling the head punch thru and then the action as I pulled it back out. I piped him a few times and then pushed in hammering away, then I would pull out a few times, then fuck a few strokes. It was great, I really liked the feel. Finally I needed to cum. I re-entered his ass and started pumping into him hard . Just before I came, he asked me to pull out and shoot it in his mouth. I popped out, yanked off the condom, and by that time, his mouth was over the head of my dick. He grabbed the shaft and pulled as he sucked my cock, and I exploded in his mouth.

Well this was some relief, and I admittedly used him a few times, but it just wasn't the same. I continued fucking girls thru college, but never found one willing enough to put my log up her ass. Some ass play was fine, but never relief. In the summer before my senior year, I was lifeguarding a country club pool. This was great as finally I was getting laid by women, not girls. Most were married, and obviously didn't have the greatest sex life at home. I was hung well, and in my white bathing suit, I attracted lots of attention. I often ogled the asses in thongs, and even some of the older ladies looked pretty good. Most of the women were in their 30's, 40's and 50's. They spent a lot of time working out with personal trainers at the club, and looked oh so fine.

My first conquest was a 44 year-old dark haired beauty with a puff of hair visible thru her tiny bikini. She had great ass cheeks and I could almost feel my rod pumping between them and then rooting in for her ass ring. I stayed semi hard most of the time, and the occasional dips in the pool showed my assets off, so when I climbed out one time and went up to this beauty, she had a hard time keeping her eyes off my crotch. I was checking out her major boobs in the tiny bikini that just covered her nipples and left gobs of flesh visible. She had been sunning most of the day, and I walked over and advised her to make sure she was using enough sunscreen.

We talked a few minutes and I went back to my chair. I could see her checking me out now and then. I made sure I let her know I liked the attention. I kept my legs open and my suit pulled tight against my dick to outline it. I would pinch it when rearranging it to try and give it some hardness. I took another dip, and took a few minutes leaning up against the side of the pool to jerk off a little. With my dick mostly hard, I got out and walked by her and headed to the snack bar. She followed. We talked some more, and she asked what I did. Told her I was a student, and she made a comment about college girls. I assured her I preferred women, not girls. She wrote something on a napkin and said if I was interested in more conversation, to come by about 8:00 that night. I looked at the napkin. It had an address. And her name, Angela.

Needles to say I was there. I rode my bicycle instead of driving as it wasn't far. I also wore my bike shorts which were incredibly revealing. They are blue with a black pouch and you could see every detail of my dick perfectly. I didn't wear a shirt. She opened the door, and looked great. She was in a white sheer wrap around thing around her waist, and her tits were tied up in the same material, spilling out. My dick began to stiffen.

She invited me in, and fixed us drinks. I asked for a Vodka Gimlet, that being my favorite drink for thinking of getting laid, thanks to my first anal partner. We headed out to her pool, and I asked why she just didn't sun here, instead of coming to the club. She said she like the scenery better at the club. I said something about the scenery not being that great, just wooden walls and a few plants, and she said "I like watching the hunks, especially the lifeguard with the big dick." Well, ice broken. I told her that if that is the scenery she was talking about, then yeah this what I liked, too. There were plenty of heaving bosoms, barely visible pussies and beautiful rounded asses to keep my happy. I sure wasn't there for the money.

She asked if I had checked out any scenery more closely yet, and I told her that I was only interested in the scenery right before me. I reached out and pulled a part of her top down, exposing on beautiful full boob. I traced a finger around the top, sides, and bottom and came ever closer to her nipple. It grew rapidly. I closed my hand over it and gently manipulated the flesh under me, rubbing my palm over her nipple. She sighed loudly, and I leaned back in my chair just admiring her one visible breast.

She said the scenery in front of her was pretty good too, and with a finger traced my dick thru my shorts. I love the feeling of my dick swelling and filling with blood. She continued to trace up and down it until it was evident that the shorts were getting too crowded in there. Man I loved this, no games, just want and need. She suggested I get comfortable, and so I stood and pulled my shorts down slowly, letting her take in the length and especially the girth it appeared. Finally, it got so low, my dick jumped out, jutting proudly in the evening air.

Kicking them off, I leaned back and began to stroke my manhood. The head is big and flares wide, the shaft was red and the veins on it pulsing as more blood continued to engorge my member. She watched appreciatively, as she played with the one exposed nipple. Finally I was fully hard and it was time for some fun. I stood up and walked the few feet to her, my pole swaying nicely. I reached her and pushed down the rest of her top. I played with her breast and nipple till it was as puckered and hard as the other. She reached behind her and her top fell off. I grabbed my pole, and ran it across her lips. She smiled as I continued to trace around her face. Precum glistened on the tip, and she snaked out her tongue to taste me. She smiled, and opened her mouth.

I guided my prick into her mouth and let out a groan as her lips closed over the head and her tongue began to dance. She was really good. She couldn't quite deep throat me all the way, but got a fair amount in and down her throat some, so I was happy. Next to fucking ass, I love being in a woman's throat and having her gag on my dick when it is lodged down it. Now most women don't like this, but this lady didn't mind. She had me most of the way down, and when she gagged, she didn't try to pull me out. Her eyes were locked on mine, and I flexed my dick in her throat, feeling her gag again. I kept my hands behind her head keeping her impaled. Her eyes sparkled. I knew this would be a good night for me. I eased out, so she could breathe, and after she sucked a few times I pushed her head down on me again. She took me, or as much as she could, and I let my dick just sit there in her throat. Flex and gag, flex and gag. Finally I needed to cum. I withdrew my rod, and went to stand behind her. I leaned her head back and pushed my rod down her throat further. Still couldn't get it all the way in, but this felt fine. I began to fuck her throat. She gagged several times, but gamely kept still as I fucked her. Finally I had to cum, so I pushed down into her, and let the spasms of cum shoot out down to her belly. She gagged several times, and I ran my fingers over her exposed throat as I shot my seed down it. She was red now, and I knew I needed to give her air, so I pulled back and shot the last few shots into her mouth. Her lips closed over the head and she sucked me dry.

I pulled all the way out and collapsed in the chair opposite. She just smiled, licked her lips and said "That was intense". We sat a few and then she went in the house and came back with a pitcher of my drink. She refilled it and we talked some more. Her husband was traveling a lot, she was horny, and she had been wanting to take a lover. Hubby was a jump on pump and roll over sort of guy, and she liked a lot more variety. I asked her to elaborate, and she did. She was pretty kinky, into mild S&M, light bondage and anal play.

She asked what I liked and I replied anything with a woman, but especially fucking a firm plump, tight ass. She looked a my dick, now semi-hard, and remarked that she was not sure about being able to handle my thickness. I told her if she had ever taken a dick up her ass, she could certainly take mine with enough proper attention. She smiled, and I knew that it was now a certainty.

We retired to the pool house and went thru the living room to the bedroom. She flung open two sets of double doors, and stood there and unwrapped the thing from her hips and let it fall. Naked, she came to me and grasped my prick and led me to the bed. After some great oral sex, and making her cum while I pounded her pussy, it was time for me to get my reward. She lay on her stomach, with her pussy on a pillow, and I proceeded to eat her ass and her pussy out. She reached over to the table by the bed and opened the drawer. I looked in, toys, lube, and hand towels. Heaven. I took a medium size vibrator out and the lube. I lubed it up, got behind her and pushed my dick into her sopping wet pussy. I put the vibrator tip at her ass and turned it on. I teased her with it, then resting it on my dick enjoying the feel, the playing with her ass again. Finally I inserted the vibrator and started pumping me and the toy into her holes. She came, and I removed my dick from her spasming pussy.

I reached in the drawer and pulled out a fairly large butt plug. Greased it up and inserted it into her ass. I slowly worked it all the way in. Her butthole clenched tightly over it. I reinserted my dick in her wet slit and leaned over her. I began to hunch my dick in and out of her gaining speed and power till I finally felt the cum reach my balls. I jammed in, my stomach against the bottom of the plug and shot my load in her pussy. She came again.

Finally I lifted off, and suggested we take a dip to cool off. She reached back to pull out the butt plug, and I stopped her. Leave it in I said. We took a quick dip, and I got out and sat on the edge of the pool. She swam up and engulfed my prick bringing it back to life yet again. I stood up, went over and pulled some cushions off the loungers, and hauled her out and onto one of them. I laid her on her back and knelt over her head and pushed my dick down in her throat again. I fucked her faced a bit, and then turned and leaned over so we could 69. I turned us on our sides, and began to eat her sweet snatch while gently playing with the plug stuck inside her ass.

She sucked and licked at me, but I don't think she was trying real hard. She was either trying not to get me too excited yet, or was concentrating on my mouth and the pink plug invading her back door. Maybe both. Anyhow, I did get her off again, and after she got her breath back, I pulled us into the bedroom. I laid her down gently, went down to her legs and lifted them. I pushed them back over her head, and knelt in front of her dripping gash and stuffed shit hole. I moved the plug around a bit and then began pulling it out slowly. She was playing with her nipples with one hand and rubbing her clit with the other. As I eased the plug out, I watched her ass slowly shut. She contracted it a few times making it wink at me. I grabbed the lube, covered my dick and pushed her legs farther back, exposing my target. I jacked my dick a few times, and then holing it behind the head, I pushed the tip to her brown ass bud. I ran my dick up and down, and then centered on her hole and pushed. Oh so slowly to savor each sensation of my mushroomed head being compressed and swallowed but her dark hole. My head popped in, and I pushed forward. I lodged a third of my length in that tight passage. She was still rubbing her clit, trying to relax as she got used to my thickness. I pulled back and pushed my hips in making her swallow half my pole up her butt. Then I started fucking in short strokes, just half my length in her. I kept this up a few, and I could tell buy her face that it was painful, but not unduly so.

Category: Anal Stories