A First Time For Anal Play Ch 1

I am the luckiest man on earth. Not only do I have one of the most erotic, beautiful, and smart women in the world, I have a woman who loves getting and giving pleasure up the butt.

Ever since I fucked my first pussy and saw that little crinkled hole so close by, I have been an ass man. As a youth, the girls who sacrificed their soft bodies to my unyielding penis, refused to yield to play involving their rectums. Mostly, I got to stick a finger in here or there as I ate them to orgasm. It was always easy to just lightly place my finger against the sphincter, and then as it pulsed as she came, I could usually get away with getting my finger in and rooting around in there. But all too soon they became aware of the invader, and they went berserk till I took it out. Of course I tried licking them and sticking my tongue in their ass holes, the girls might like it, but they generally refused to kiss me later if I had frenched their shit chute. That was to change, but it took a woman, not a girl.

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I was 18, she was 41. Jesus she was hot. She was a very wealthy woman here, with her own sports entertainment company, including the local minor league baseball team. I was at a game with my parents and neighbors. One neighborhood girl was after me, and had been teasing me for months. At the ballpark, she had cornered me as I came out of the bathroom, and pushed me up against the wall and began to kiss me. Her hand reached under my shorts and locked on to my dick, tugged it a few times, still trying to kiss me. Well I hated the girl, but I was 18, with a prick that would fuck anything basically. I got hard, she got excited, and she asked if she could give me a blow job. Well shit, somewhere in the back of my mind, I knew it would cause problems later, but for now I needed to blow my wad.

She took my hand, and led me to an area by the outer wall where there were some trash cans. There was a waist high wall around them, and she simply pulled me in, squatted down, pulled my shorts down and engulfed me. That's easier said than done, for I have a very thick penis. It is only around 7 inches, but the thickness makes it appear to be a bat. She did good though, getting me in her mouth, scraping against her teeth and letting me in to the back of her throat. I came as I felt her gag around my dick again, as I shoved my thickness further down her throat. She spent a few minutes, licking me clean, and finally I tired of her. I turned around, pulled my limp dick out of her mouth and hands, and there was this incredibly classy older woman, in a beige business suit standing there with a half smile on her face, just staring at me. I shrugged, and smiled back and pulled my shorts up over my dick and hurried back to our seats.

After the game, I was wandering around behind my parents as they stopped every few minutes to talk to friends and acquaintances. I mumbled hi now and then, paying no attention. Until that is, they stopped to talk to the woman who had seen me tucking in my penis. My parents introduced us, but I didn't even hear her name, she was fucking gorgeous closer up. She wasn't model beautiful, but there was something exotic about her. She reeked of class, money and somehow sex. I thought about her seeing my limp dick, and my dick jumped. She came toward me, my dick rose more, she took my hand, God was it soft, and told me to come by her office some time, and she would make sure I got some complimentary tickets to some games for me and my friends. I thanked her, and she turned around and said a few more words to my parents and their friends. When she turned, she somehow backed closer to me, and as she turned, I felt her hand brush across my now mostly hard penis. It jumped again, and as she stood there a sec, I could smell her hair, and feel the heat of her body so close. As I was standing there engrossed, her other arm had snaked behind her back, and she pressed her hand backward, and touched my straining dick. She grasped the pole thru my light shorts and gave me a few pulls. The she was gone. I was left speechless, with my monster dick tenting out my shorts. After I could finally breathe, I turned sharply, hollered I'd meet them at the car and hit the bathroom. I grabbed my dick thru my shorts, and pulled at my dick as she had done. I closed my eyes and imagined her hand wrapped incompletely around my manhood and I pulled and pulled. The fabric sliding over my shaft felt sooo good. I saw her face in my mind, and that half smile and those full lips, lips I wanted wrapped around my dick, and awww shit, I was cumming. I yanked my shorts down as it began to shoot, wasting my seed in the toilet, yet seeing it shoot in her mouth in my minds eye.

The next day, there was a game, and I actually paid for it and went alone. At about the end of the 4th inning, I worked up the nerve to go find her and her offices. She wasn't there. I explained to the girl sitting there that she had told me to look her up, so she told me where she was sitting and I headed off to find her. As soon as I stepped in the box, she stood up and excused herself from the group of men gathered around her. " I promised this young man some tickets", and she left with me in her wake. We hit her offices and went into "her" office, closing the door behind us. She was pleasant, but cool to me and asked if I like the team, the game etc. How long had I been coming, how many tickets I needed for friends etc. She was a bit scary. So in control. I could hardly mumble my answers.

Her secretary buzzed her, she said something to her, and then she cut the connection and came around to the front of her desk, standing about 3 feet from me. She asked if I found her attractive and I answered affirmatively. She then told me to pull down my shorts. I just stood there with my mouth open. She repeated more firmly "pull down your shorts and show me your penis." I unwittingly obeyed. This time I was wearing a jock strap, I had been too afraid I would tent my shorts like last time.

"Show me your penis" she repeated.

I had begun to get hard. I tucked my thumbs in the top of the jock, and pulled it over my dick. It sprang out semi-hard.

"Does it get bigger?" she asked.

I nodded, and she told me to make it fully hard for her. I gripped the shaft and began stroking, no conscious thoughts in my head, just obeying this sexy, but intimidating woman. I pinched the head, and reached under to massage my balls and I was fully hard.

"Would you like to cum?" she purred.

I nodded again, and she turned around to her desk, and picked up a card, and some tickets. "Call me at this number tonight at 11:30 sharp. Now tuck your penis back in and close your mouth." I did as told, and she went to the door, opened it and stepped thru. I followed.

I rushed to the bathroom again and jacked off, then found my seat and watched the rest of the game. Actually, I watched the box she was sitting in. I could just see the top of her head mostly. The game passed quickly. It was about 5:30 now, and I was wandering home wondering if I had the nerve to call. I got home and was contemplating jerking off again, but decided I needed to be ready to perform tonight, so I held off. It was pretty tough not touching myself as all I could think about was the possibility of fucking this gorgeous woman. I got thru the rest of the night, going out with the guys, watching some baseball at the bar. I wasn't drinking, or watching the game. Or paying attention to the guys. They noticed and ribbed me pretty good, but finally it was 11:15. I got up told them I was off, and went outside. I pulled the card out of my wallet, waited till my watch said 11:30, grabbed my cell, and dialed. She answered. She told me where to come, a very expensive condo downtown. I wasn't far. I knocked on the door, and she opened it, dressed in a thin short T-shirt and sweats. We made small talk, and then she got to business. She asked if I had much experience with women, or just blowjobs at the ball park. I stammered and stuttered and admitted I had had some experience. "Girls", she said "were different from women, and she was going to show me how to make love and satisfy a woman."

Again, she coolly ordered me to stand up and pull my shorts down. She told me I was to masturbate and cum in the glass she pointed to. She said that after I had come, I would be able to pay better attention, and last longer. I was so fucking hot and so incredibly confused. I wanted to get to her and fuck her, not jerk off. Nevertheless, I did as I was told. I began to pound my meat for her and eventually I got in to it. I was getting close when she began to touch her breasts thru her shirt. My dick jumped and swelled more, and I began to get off in earnest. I was getting close, and she grabbed the bottom of her shirt and began to lift it over her head. Her breasts emerged. Not big, but so beautiful. I don't know what size they were, but they were a perfect handful with dark brown nipples that were small and puckered and hard.

I came.

As I started to shoot, she looked hard at me and said "the glass". I grabbed it, put my dickhead in it and shot rope after rope of jizz in it. I squeezed off the last drops and stood there, my dick softening. She came to me and took the glass from me and proceeded to down it. My cum slid slowly towards her lips and finally ran into her mouth. It was so gross and sexy at the same time.

She licked her lips, told me to undress completely, and she stood and watched. As soon as I was totally stripped, she came to me and kissed me. Soft, but firmly. I finally broke my trance and began kissing her back, hard. I could taste my cum and it was kinda yucky, but mostly I was just aware of her lips and her hard nipples and her sweatpants pressed against my limp member. She broke the kiss and told me not to be so rough, to kiss her gently, and concentrate on the feel of her lips and tongue. I relaxed a bit and did just that. After kissing for a few minutes, she slid out of my embrace, and took my hand and led me out to the patio. There was a double wood lounger thing. She laid back on it, and motioned for me to get beside her.

I laid down next to her, and she took my hand and placed it on one of her breasts. I began to squeeze it and she placed a hand over mine and told me to be gentle. "Touch softly and explore" she said. She guided my hand over and around her breast, then cupping it and squeezing, then moving it over her belly, up the other side and over and around her other breast. She let go, and I continued to lightly stroke her entire front and sides, coming back to her breasts to squeeze them and then roll the nipples in my fingers. Finally, she took my head and pressed me to her hard nipple, and I took it in my mouth. I suckled it like a newborn, feeling how hard it was in my mouth, and how soft it was around my mouth and chin and nose. I got up over her kneeling and began sucking her other tit as my hand roamed the other side. She was breathing heavily, and beginning to move under me.

I became lost in the feel of her in my mouth and hands, and I touched and sucked at her as if I had never done this with a woman before. I was sucking one nipple, and she whispered "bite it gently." I took it in my teeth and bit softly. I rolled the other one tighter under my fingers. "Harder" she moaned. I bit down with more pressure and she began to writhe under me. I moved over her other tit and began to bite that one. I bit harder, and she squirmed even more. I bit at the other one, harder now, and she began to pant. I felt her hand move between us, and she began moving her hand over her clit, rubbing my dick in the process. I began to grow. Her movements grew more frantic, and I bit down on her nipple pretty hard, then bit the other one. Her arms wrapped around me and she pulled me to her. My dick was against the crevice of her pussy and I began to grind at her. She began panting, and I bit down again hard and quickly bit the other. She came. She arched against me and began pounding up at me in short strokes. Her nails were etching my back with lines of fire, but it felt so good. She shuddered and then lay still under me. I pushed upwards and kissed her. We made love to each others mouths a moment, and I realized I was making love, not just fucking. I had made a woman come with my mouth and hands, not my dick. I felt so powerful.

I broke our kiss and began to softly kiss her nipples, moving down her belly. I started pulling down her sweats, and continued kissing down. She arched up, so I could get them down, and I was greeted by the sight of my first shaved pussy. Holy shit. I continued licking and kissing down, till I was licking into her crevice. She was so hot, and wet. She pushed me up, and said " I need you to put your penis in now. Nice and gently, fill me up and make me cum." I got up, pulled the sweats off, and laid on her again, kissing her face and mouth. She wrapped her legs around me, and I lifted up a bit. She reached down and guided me into her wet pussy. I pushed in slowly. Jesus it felt good. Usually I was trying to ram in and get fucking. This was different. I felt her open up to me as I pushed my way in. She was so wet, so hot, so tight. I was in all the way, and just pushed against her as deep as I could holding myself in her. I could feel her pussy working over me. It was exquisite. I pulled back, just the head in and slowly pushed in again. I fucked her like this for a few strokes and then began to fuck into her harder. Finally I was pounding away in this pussy old enough to be my mothers, and I felt her tighten on me and begin panting again. "Fuck me harder, fuck me harder you dick" I obliged, and tried to put more force into my strokes and her pussy. I leaned forward and took a hard nipple in my mouth and bit, hard. I felt her shake, and I bit the other, and her fucking pussy went wild on my dick. Squeezing and tightening and I felt my nuts squeeze as unloaded again and again in her womb.

I lay on top of her for a few minutes, enjoying the feel of her pussy wrapped around my cock. I nipped gently at her tits again, and was rewarded by contractions around my dick. Finally, I knew I was getting heavy on her, she arched up against me, kinda rolling me off to the side. My dick left its warm cavern, and I plopped back, breathing hard. We lay there for awhile until we could breath normally. She got up, went inside and returned with drinks. I don't know what it was, but it tasted tart and good. "Vodka gimlet" she said. To this day, I still drink those and fondly remember the first taste, lying there with this older woman beside me, my dick wet and soft and drying in the chill breeze.

We just lay there. I finished my drink, and didn't know what to do next. She finally put hers down, and went back in and came out with a warm washcloth. She proceeded to clean my genitals, and then told me to stand up. She reached in a cabinet, and pulled out a vibrator, and some KY jelly. She told me to get my dick hard again. Damn, I wanted to get hard in her mouth. I leaned forward, pulling on my spent prick, and aimed at her mouth. She gave me an icy stare and said to stop fooling around and masturbate for her. I backed off and took my dick in hand. While I was stroking, she was messing around with her toy. She lubed it up, spread her legs, and instead of putting it in her pussy, she turned it on, and rubbed it over her crinkly asshole. I felt a rush in my dick as I began to swell. I began to jerk in earnest. She teased her ass a bit, and finally stuck it in a little bit, pushing against that tight hole until the smooth tip slid in. My dick jumped in my hands as I watched more of it disappear into her butt. She began slowly fucking herself with this smooth purple invader. More and more of it disappeared. Finally she had all of it in except for the base of the thing. She turned the ring at the base and the humming got faster. She held it inside her, just letting it hum. My dick was now a steel battering ram, and I needed to get it inside her. Her eyes were closed as she held it tight inside her rectum. I reached out and touched a breast, cupping it in my hands. I began thinking about how much I wanted to put my pole inside that brown hole. My dick jumped again, and I swear I was a big as I had ever been. She watched my dick jump, and smiled, and removed the purple dildo slowly from her butt. So slowly. I watched as the length slid out of her, and finally the taper began to narrow. Her sphincter clamped down on it hard, slowly getting smaller as she slid it out. Finally, it popped out completely, her fucking ass, open for a second, before slamming shut.

My eyes were huge, my dick was huge, and my heart was hammering so hard, my dick was pulsing with it. Please my eyes begged, let me put my prick in your butt. Please let me slid my pole inside your fucking bowels. She seemed to read my mute pleas, and looking straight at me, she asked

"Do you want to put your dick inside me there?"

My dick twitched again in answer. Like a zombie, I moved to the bottom of the lounge, and stroked my dick, as I looked at the brown bud I had always been so fascinated with before. I was finally going to stick my pole in a woman's butt. I moved toward her, clambered over her, and pushed up to my knees. My dick was a few inches from her pussy and ass bud. She reached down, got the lube and squirted some in her hand. The she sat up, and began stroking my steel rod with her soft, slick hands. That was heaven itself. After I was completely covered in the lube, she pulled her legs back over her head and said "Take my ass, go slow, you are too thick to just ram it in, but if you go slowly, my sphincter will stretch and you can get it all the way in." My dick was pulsing with my heart as I inched forward, the tip nearing her puckered ring.

Finally my dickhead rested against her butthole. I leaned into it, trying to push it in. My dick began to bend. I grabbed it behind the head and pushed again. Jesus, the sensation as those crinkly ridges began to stretch over the tip of my dick, parting around it. My head was almost in, and the pressure was so intense over my cock head. I pushed a tad, and my whole head was in her butt. She was gasping, totally still, her nipples bullets on her breasts. I had to move. It hurt to stay still like this, it was too tight. I pushed farther in, watching my dick slid another inch into her tight shit hole.

She was breathing in short pants as I inched in. I had about three inches in, but had to pull out a little, the pain form the constriction around my dick was just too much. I eased back out, and watched the ass ring contract as I pulled the head out. I just looked at that crinkly hole, and wondered that it had stretched so much. I put my dick back against the opening, and pushed in again. It was significantly easier this time. My cock head popped in and I pushed in deeper going about 5 inches in. She gasped loudly and jumped slightly. I pulled back till just my head was in. I fucked into her slowly, enjoying the tightness and the heat that enveloped my cock. I continued fucking slowly until finally I was balls deep in her ass. I pushed hard against her enjoying the feel of my entire length lodged up her butt. I began to move back and forth, sawing my fuckpole in and out of her rectum. At first it had been so tight, that I couldn't have cum if I wanted, but now, it just felt good, and my balls tightened up, and I knew I was on my way to an incredible orgasm. I was pounding into her pretty good now, and she was lifting up to meet me. Every once in awhile, I stopped, straining as far inside of her as I could, and then slowly withdrew, watching my dick appear as it slid out of her.

Next thing I knew, she was pushing me off. Shit, I needed to cum in her ass, she couldn't make me stop now, I piled back into her ass brutally jamming my length fully inside her. Her eyes got cold, and she told me to take my cock out. I stared her down a sec, but then withdrew. I watched as my dick head plopped out. Her hole stayed open. Shit, I had sure stretched it out. She turned over, and lay her head down on the lounge. Her ass was in the air, her asshole open and red.