Anal Summer Ch. 01

"I could tell," she said. "It shows," again fluttering her eyelashes and biting her lip.

I was amazed to find out that Madison's just purchased, swanky new condo was about three minute's walking from where I lived with my folks in a family-owned apartment building. The contrast made me feel small. Walking past, I thought it best to keep this fact to myself for the time being.

With the fresh sea air blowing in from the harbor, the boats bobbing in the tide across from us, we had reached our destination. Waiting for Madison to unlock the door and invite me up, the butterflies in my gut grew larger and more abundant. When she turned to me and asked if I would like to see the place and have a drink, I was relieved. I said I would love to.

Madison motioned me to follow her in. Once inside, I was both impressed and envious. The place was something I would dream about living in. "I'll get us something to drink. Sit down and relax," she said. Turning down a corner, she disappeared, only to ask from wherever she was, "Is wine okay?"

I said, "Yes."

She returned with a bottle and two glasses, putting them down on the coffee table before me. Then she said, "Just a second. I've got to get out of these shoes." And just like that, she was gone again.

I was still in awe over the "cool factor" of Madison's condo. It was roomy with exposed brick and shiny hardwood floors. The furniture matched Madison's sophisticated style. I thought to myself, "If I don't get any pussy......I'll just fuck this couch."

When Madison returned, she was wearing a very sexy black sheer robe with a matching teddy underneath. The robe was full length and had lacy black frills on its edges and sleeves. Practically see-through, the teddy was a sight to behold as well. Her body was curvy and slightly thick but not grossly voluptuous - a complete vision of sexiness and womanly charm.

Seductively bending over in front of me to pour two glasses of wine, her plump ass was just inches from my face. Madison took both glasses, handed me one and then sat beside me on the couch. There, sitting almost sideways but cross legged, staring at me over her glass, she caressed the glass and its stem. I was speechless. She took a sip of wine, scooted closer,and leaned up against me. Putting her face toward my neck, she was so close I could feel her breath on my skin.

"You smell really good," she said, then added, "I thought you'd smell like that kitchen."

"I showered in the employee locker room," I replied.

"There's a shower there? Had I known, I would have come in and rubbed soap on your back," she teased, and took another sip of wine.

I couldn't think of anything clever to say to that and began to feel overmatched and in full free fall, thinking I was blowing my chance. Madison sensed something, placed her glass down and got up, again giving me another look at her wonderful bottom. She then walked behind me and stated to rub my shoulders. Her touch felt good, her hands soft.

As she massaged my neck and shoulders, she said, "You're far too tense. All that hard work at the gym, and then the restaurant has you all in knots. My, what a fine physique you have," she whispered as she rubbed.

I tilted my head back to face those beautiful eyes and alluring voice. "Thanks," I started to say. Before I could finish my reply, she kissed me. Deeply. She crawled over the back of the couch and continued to kiss me.

I wrapped my arm around her and untied the robe with my free hand. With Madison's tongue intertwined with mine, I reached for her thigh, slowly moving my hand up the leg to her vagina.

I moved away from kissing her and nibbled her neck, making my way to her enormous tits. Madison was stroking my cock through my pants with the palm of her hand. I was using my index and ring fingers to spread the lips of her sex and then began to tickle her swollen clit with my middle finger.

She had managed to unbutton my fly, push down my jeans and free my erect hog and balls. Her caress on my cock and ball sac was just enough to make me want her more but not bring me too close to coming.

In that time, her cunt began to get very wet. My fingers, now soaked in her wetness, did their job on her. Madison began to gyrate rhythmically with my fingers. Than, all at once she put both hands on the sides of my face and said, "Come with me." She arose, grabbed my wrist and pulled me along with her. She walked me through the kitchen and dining room to a hall that led to her bedroom.

Still holding my wrist, she turned on the light, and I wound up with my back to her bed. She shed her robe and teddy while I undressed myself. Pushing me down gently by my shoulders, I was put into a sitting position on the bed with her large tits at eye level as she stood before me. Madison seemed to be ten feet tall at that point and in complete control of me. Lurching forward, I buried my face in her bosom, frantically sucking and thrashing my face in her tits and groping her bottom with both my hands kneading her buttocks.

Again taking charge, Madison climbed on my chest, pushing me backward onto the bed while sliding and grinding her wet snatch down my torso. She was lying on top of me when we finally came to be face to face, and she planted another deep kiss on me, clutching both my wrists over my head while pinning me to the bed.

She whispered in my ear, "It's a process, Lawrence." Then, with a pregnant pause, she whispered in my other ear, "And it's a process of pleasure." Her soft voice and breath in my ears sent shivers down my spine and gave me goose flesh.

"You must learn to relax, savor and enjoy it," she continued.

Calmed by this, I lay motionless, glad to let her - the more experienced one - lead the way. Though my ego was slightly affected, I let those thoughts slip away as Madison took over. As she kissed my neck, she caressed my arms and chest softly, barely even touching. First it was the tongue, then a kiss, and then another little bit of tongue. That was her technique as she worked her way down.

Lying on my back with my legs off the edge of the bed with knees bent, feet touching the ground, she knelt between my legs. I felt her mouth and tongue on my ball bag. With one long lick she went up the length of my hard dick, teasing me with her mouth, and then she took every inch of it down her throat. I was blasted away by this! It wasn't that I'd never been sucked off before, but I was still under the impression that you had to work on a girl for a long time to get her to suck you. A blow job on a first time was a foreign idea to me. I'd always had to wait in relationships for a long time before a girl would bestow oral pleasure upon me. My youth and ignorance were apparent to me even as it was happening.

"So you didn't need to go steady to get your dick sucked," I thought to myself.

With a flat, open hand she gingerly lifted my swollen balls from the back and gently pushed them toward the base of my throbbing meat pole. Then, taking a long, slow, deep, fluid swallow, she made my manhood disappear once again. Down, down all the way, down deep, and then holding me there for a long second. Coming up in ultra slow motion. The way she lifted my scrotum while she made long, slow passes up and down my cock did something to intensify the sensation.

There was no doubt this woman was good with a dick and had seen plenty of them. Then, all at once, she started to ratchet up both the suction and speed, bobbing her head more vigorously and sucking down with more energy.

Madison's hands were also more active. As she sucked me, she began to caress and tickle the underside of my seed bag, slowly roaming to the little place where the scrotum ends and the anus begins. This was a new sensation, and my inexperienced and inhibited mind was getting in the way again. Her hand held my balls, her mouth owned my hog, and her fingertips were inching toward my asshole.

Part of me was saying to my self internally "You can't let her touch your asshole! You're a man!" but the other part of me was in complete ecstasy. Both sides of my brain came to an agreement: They agreed to stop her hand and the blowjob as well for fear that I might come before I got to fuck her.

Covered in sweat, I lightly directed her head up until she took my tool out of her mouth. She looked up with her beautiful eyes and quickly got the hint. She arose and then lay beside me.

I turned to her and asked, "Do you want this?" as I placed her hand on my stiff member.

"Yes," she said, never looking away from me.

"Then what shall we call it?" I teased in an attempt at sexy pillow talk.

"Your cock," she answered in her soft alluring way.

"And what about this?" I asked as I stroked the lips of her vulva with my fingers.

"My pussy," she replied.

Almost involuntarily I blurted out my first dirty talk. "I want to fuck your pussy."

Madison just smiled and cooed. Feeling relaxed and unashamed to talk dirty felt liberating and free. In fact, I liked it and loved the fact the she was getting off hearing me say those words. She talked right back at me.

"All the men I fuck are older than me when all I want is a hard, young cock. Sure, they have money, and they can keep it! I wanna get fucked again and again all night," she purred to me like a seductive cat.

I offered, "So you don't mind that I'm nineteen," instantly regretting having said it.

"No, I want to have you because you're nineteen," she retorted, her dominant personality taking control of me again. I was putty in her hands. She was the boss, and I no longer cared.

"I'm thirty-five," she said, shifting her eyes toward my hard-on and gesturing at it with her chin, "and you don't seem to mind. Why should your age bother me?"

The room was steamed up by our sweating bodies.

The glorious smell of her pussy juice mixed with her perfume and our sweat hung in the air. I spread her thick, shapely legs. I mounted her in the missionary position, looking down at her steaming cunt, glistening with her wetness.

I slid my cock into her hot, wet pussy, wrapping my arms around her for leverage, then launching myself into her as hard as I could, finishing the move with a hump and snap of my pelvis. I would repeat this over and over til the end - A power fuck as hard and fast as I could.

Madison's moans and whimpers were spurring me on. I could tell she hadn't had her honey pot slammed this hard in a long time, if ever. This was hard, hot and wild sex. It was all I knew. As a rookie in the art of fucking I thought this was the best and only method in which to satisfy a woman. It seemed to be working. Again, in my ignorance I managed to find just what she wanted. The moans and screams were nice to hear. She had taken over, and I felt she needed to know that I was the man and I would do the fucking.

"You like getting fucked, don't you!" I grunted.

"Yes.... keep fucking me!" was her almost breathless answer.

Our bodies, now dripping in sweat, made a slapping sound when my hips collided with hers. The aroma of her steaming cunt reached my nose.

"OHHHH, that's it! Fuck my pussy hard!" She could barely get the words out. Then another series of moans and screams of passion accompanied that wonderful slapping and slurping sound our bodies made. My prick and balls were soaked in her juices. I continued to ram her velvet lined twat for some time. For the first time I was in control, and she had lost her composure. She was overwhelmed with pleasure, and could not form the words to speak, only breathless moans and coos.

Wanting a change of pace, I withdrew from her and nudged her to flip over.

"I want you on your knees!" I commanded.

Madison obliged, flipping over without a word.

"I'm going to take you from behind," I told her in the sexiest tone I could muster. The view from behind her was amazing. I entered her cunt and started to plow her again as hard as I could. After a short time we worked out a nice rhythm, where she would push her twat back to absorb the full impact of my thrust.

"My pussy hasn't been fucked this hard since college!" she appeared to be thinking out loud. For someone who implied that her sex life was very active, Madison's vagina was still tight. She was facing the headboard during our doggie style romp. After a while, without explanation, she slid forward and my tool fell out of her honey pot.

"What's wrong?" I inquired.

"Nothing ... just a second," the words barely escaping her mouth. She was leaning forward and reaching for something.

By the headboard, there was a nightstand with a lamp. I thought for a second her aim was to shut or dim the lights. Instead, she was reaching for the little knob on the drawer of the nightstand. What she retrieved out of the drawer almost made my heart stop. A full size tube of K-Y jelly was now in her hand, and she was handing it back to me as the moment of surprise and joy struck me like a ton of bricks. Was this what I thought it was, what I wished it was? I thought I had better check first but didn't want to scare away the moment. Thinking quickly, I managed to play dumb: "Your pussy is so wet. We don't need this."

"No!" she said, again with authority in her sultry voice. Then she uttered the words I thought I'd never hear a real woman say to me: "I want you to fuck me up the ass!" It was a moment that I would cherish the rest of my days, a moment I had wanted somehow before I even knew anal sex existed. A moment that I fantasized about and masturbated to countless times. An act I desired since the day I saw that first porno at my friend's house. I wanted to drink in this moment and make the most of this fantasy-come-true.

I gazed upon her welcoming, sweat-soaked buttocks shining like two hot buttered globes. She peered back at me over her shoulder, still on hands and knees while I was visually taking in the beauty of her round firm ass and its lovely crevice, following the crevice down to the wrinkled pucker of her asshole and her battered pussy lips, glistening and dripping with her sweet honey.

I squeezed some K-Y on to the head of my cock and slowly spread it down its length. Madison said, "That's fine. You need to lube up your cock, but let's start with your fingers first." She told me that a light massage on her lower back and bottom would help her to limber up and get loose. I obliged, thankful for the break.

Rubbing her waist and lower back was a sensual experience for me, too. Especially when I worked my way to her beautiful ass, kneading her buttocks, spreading her cheeks and massaging them open and closed. It was like playing a pornographic game of peekaboo with both of her fuckholes. This allowed me a chance to rest and recover so I wouldn't come too fast, while keeping the mood sexy and erotic.

I then got the K-Y jelly ready. Spreading her ass, I rubbed her sphincter, teasing it with my fingertip staring at her asshole. The mystery and darkness of it , the naughty taboo of it, made me hot and want to get down to business. I squeezed out a liberal glob of it and placed it on her bung hole, plastering her rectal pucker, caressing and spreading it in circular strokes, slowly putting more and more pressure on her asshole until the tip of my index finger was in it just past the first knuckle.

"MMMMMMMMM... now we're getting somewhere," she acknowledged in a breathy voice. With slow, steady pressure, I worked my lubed finger in her ass as far as it would go. "OHH, Ohh that's it right there." Madison instructed. "Keep your finger there ...... feel my muscles relax and open slowly," she added, now fully enjoying the insertion. "Now your middle finger, too," she moaned.

I noticed that unlike finger fucking her pussy, she enjoyed anally the withdrawing of the fingers more than the forward thrusts.

This continued until we were up to three fingers at once. Satisfied that Madison's nether region was lubed and loosened adequately, I readied myself with more lube and was ready to mount her, stealing another peek at her sphincter, now visibly more open than before. Madison herself ready on her hands and knees and wiggled her hips as if daring me to take her from behind.

I had a little trouble getting in her backdoor, my inexperience showing again. Madison reached back, got hold of my erect hog and guided me up into her ass, a procedure that always made me horny when I saw it happen in porn films. Then, with the swollen head of my penis breaching her ass, she pushed back slowly as I pushed forward. I penetrated her deeper and deeper until I was balls deep, and the pink ring of her sphincter expanded fully accommodating my entire tool. Her forbidden passage was open and receiving my tool. It was so tight and hot. It felt better than anything I had ever before experienced sexually, even better than her pussy.

Madison looked over her shoulder and said, "You'll have to take it a little easier than when you were in my pussy, okay?" adding, "at first." and, "when I tell you I'm ready you can go ahead and fuck as hard as you can."

"Is that good?" I asked. "Does my cock feel good up your ass?" I spat out nervously, also trying to talk sexy again as well.

"Oooooo Yeahhhhhhh," she answered in more of a moan of ecstasy than an actual word.

Having always been visual, I had to look down and behold the act I waited my entire life for. Looking down and seeing her musky hole stuffed with my veined rod sliding in and out was a wonderful vision. I noticed that Madison was also masturbating in time with my hump stroke.

"Now I want you to fuck me harder and slower," She instructed, "and when you're all the way up in there, keep it in for a while."

I fucked as I was told . Who was I to question? Until now, I was an anal virgin, and so far she had been an excellent teacher and an even better fuck. It was everything I had imagined, and more. Every slow, hard stroke was complete, sinful joy. I had read quite a bit about backdoor bonking and knew that the rectum is full of nerve endings and several muscles and a major artery. Done right, ass fucking can be great for all involved. The muscles would account for the heavenly tightness, and you could also feel the artery pulsating.

Madison was starting to talk dirty and moan. "Fuck me harder! Ahhhhhh, yeah, ohhhhh! OOOOOOooh, fuck my ass harder!"

"Like this?" I asked, as I impaled her elastic sphincter with more fervor!

"Your fucking cock feels so good in my ass! Ahhhhh it's soooooo big! It's sooooo deep!"

These were the sounds of a woman near orgasm. By this time, I was taxing her asshole as hard as I was her cunt before. Her masturbating also intensified.

"AHHHHHH, I'm coming!" she screamed. Her tight asshole was gripping my cock even tighter, pulsating and spasming with her orgasm.

This was what pushed me over: The thought that a woman would have anal sex, coupled with the thought that she enjoyed a cock in her ass so much that she could come as a result. My own toes started to curl and my feet and calves seized up. My heart felt like it was going to explode. The wonderful electricity ran from my heart down my body to my hips simultaneously with the same electricity running from the balls of my feet, up my calves through my thighs to my hips where it exploded through my own rectum, which seemed to clench up, through my testicles then finally out of my cock . My hips began to buck and hump involuntarily as if I was some sexual marionette controlled by an unseen puppet master pulling my strings. I filled her rectal cavity with my hot semen.

She must have felt this happening. "Yes! Yes! That's it! Fill my ass with your hot come!" she demanded. I obeyed, squirting load after hot creamy load and emptying the entire contents of my balls in to her naughty place and then collapsing backward. Still trying to catch my breath, I looked over at Madison. She was still face down, ass up and still pawing at her cunt, her gorgeous ass covered in sweat. Her asshole was agape like a glazed doughnut frosted with my milky white cum. I lay there, my entire body tingling with sensation, still recovering from the most explosive orgasm I ever had. Madison, too, was frozen in her position as well. She had stopped touching her clit and now the only movements were the deep breaths she was taking. With her ass cheeks still aimed skyward I watched her asshole's aperture slowly shrink, like a closing magical portal to the dimension of ecstasy, as my creamy jizz dripped and bubbled out of it.