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The Weekend - Part Four

Gail's first experience with anal sex
After Gail had enjoyed the aftermath of her orgasm, I reached out for her hand and led her to the bed.

Gail sat while I undressed. When my manhood popped out, she stared at it.

“Mmmmmm,” was all that she said.

I never concerned myself with questions of a big versus a small cock. A woman knows what she likes. And, much depends on a man’s ability to satisfy his partner, whatever his size. That being said, it has been my experience that a large erection makes for at least an enjoyable visual experience for a lady, if nothing else.

I have a big cock; eight and a half inches and thick. Woman have stared at it, laughed at it, complimented me on it, measured it, played with it, photographed it, and drawn pictures of it. Most important, women liked it.

Gail held my swollen organ in the palm of one hand and stroked its length with the fingers of her other hand. Pre- cum streamed out of its little eye and fell onto her hand.

“Can I play with it now?” she asked.

“For a little while,” I said.

Her mouth engulfed the enlarged head. For a minute or so, Gail sucked and licked just the sensitive head, while stroking the shaft. Her mouth was warm and wonderful.

I slid my cock from her mouth, leaving a string of saliva from her lips to the tip of my erection.

She moaned with disappointment.

I lay on the bed and told her to sit on my cock. Her momentary disappointment was replaced by a smile and girlish excitement.

Straddling me, she held my long shaft in her hand, and maneuvered the engorged head to the opening of her wet pussy.

Lodging the head of my cock at her opening, she pushed down.

Slowly, inch by inch, my manhood slid into her wet hole. Three times she had to stop to let her pussy adjust to my girth, and to relax her vagina’s grip on my cock

“Mmmmm, I like this,” she said, as she put both hands on my chest and slowly moved her ass up and down, sliding her slit on my shaft. “I like this a lot.”

When she was comfortable, I increased our pace.

Her facial expression turned from apprehension and caution to pleasure and desire.

I rolled her onto her back, lifted her legs up, bent them back at her knees, and re-entered her. I kept a faster pace, eventually extending her legs up straight, holding her ankles by my shoulders while I continued to fuck her.

Her breathing was labored, she pulled her nipples, her eyes were closed, and her expression indicated that she was enjoying the pleasure that was again consuming her body.

She was now taking my full length, my balls slamming against her ass.

I flipped her over onto her hands and knees, telling her to arch her back so her slit was fully exposed for the taking.

I wanted to fuck her doggie.

Immediately, I noticed a problem.

Gail’s legs, from knee to hip, were long. When I was kneeling behind her, my erection was a good three inches below where it needed to be.

To fuck Gail doggie, she was going to have to spread her legs farther apart so that her love hole and my cock would be at the same level, or I was going to have to partially stand.

Once that problem was solved, I slid my cock back into her well lubed fuck hole.

This was likely the last position Gail was going to experience, at least for this day. I wasn’t going to last much longer.

Gail turned her head to look at me, and said, “God, that feels good. Fuck me harder, fuck me harder.”

I grabbed Gail’s hair with one hand, pulled her head back towards me, and slammed my cock into her wet opening.

“God, yes!” she repeated over and over. “Fuck me! Fuck meeeeee, yesssss!”

Beads of sweat appeared along her back, and traced down her spine as she arched her back. She pushed harder against me, wanting to get every inch of me into her aching cunt.

Gail looked back at me with a lustful look, her eyes half closed, biting her lower lip.

Sometimes a woman has an expression on her face that is so sensual and carnal that the look alone can cause a guy to cum. This was one of those times. I prepared to shoot my gooey load all over her back.

Before I surrendered to my need for release, however, I wanted to give Gail a small introduction to anal sex.

I wet my thumb and ran it lightly over and around her puckered hole. There was an unmistakable response.

She liked it.

Encouraged, I slid my thumb into her asshole up to my knuckle while I continued to slide my cock into her wet pussy.

“God, yes! God, yes! Yes! Yes! Yes!” she moaned.

Her face was crimson. Her teeth clenched, she grunted and groaned with pleasure, and she was getting ready to cum again.

I was ready to explode.

“Fuck me in the ass!” she yelled. “Fuck me in the ass!”

Her demand was not expected.

Gail and I had discussed anal sex, the need to have her well lubricated, and how she had to be comfortable and relaxed in order to accept my shaft in her ass. And, we had discussed why that process took time, particularly for a lady new to anal sex.

While she wanted to be fucked in the ass, she was not ready, and I did not have the necessary "tools" at hand.

I told her that we had plenty of time and could do anal the next day or the day after. We would take our time and it would be a pleasurable, positive experience for her.

She turned to look at me. Her steely glare made it abundantly clear that she wanted to be fucked in the ass, and she wanted it now!

I pulled my cock out of her slit and jumped to the bureau to grab the lube, her vibrator, a condom and the hair brush.

“Hurry! Hurry!” she said.

Returning to the bed, I moved behind her and slid my prick back into her pussy, fucking her doggie, while trying to open the bottle of lubrication.

I fucked her slowly while I told her that we needed to get her prepared, as we had discussed.

I asked if she was ready.

There was a quick and impatient response. “Yes! “

I dribbled lube on the crack of her ass and let it run down over her asshole and pussy, and drip onto the bed.

I slid my cock out of her slit, and positioned myself so that I could insert one finger and then two into her asshole, slowly sliding them in and out, twisting them, until I felt her sphincter begin to relax.

I lubed her vibrator, turned it on, ran the humming toy over her hole for a minute and then slid it slowly into her ass until only the black base was exposed.

The more the vibrator slid in and out of her ass, the more relaxed she became, and the more she moaned with pleasure.

I grabbed the condom package and ripped it open with my teeth.

All this time, while I worked to relax her anus, my cock had become more limp than erect.

Putting a condom on is difficult enough. Putting one on a limp cock, especially while trying to keep a lady's asshole open and wanting, is near impossible.

I stroked my shaft to get a full, hard erection again.

My mistake was using my oily hand to stroke my cock.

The condom easily slid on because of the lube on my now stiff shaft; it also easily slipped off for the same reason.

If getting my cock into Gail’s pussy took some patience and effort on her part, getting my rod into ass her was an even more difficult task, even under the best of circumstances.

I moved Gail to the carpeted floor and had her get on all fours. At least on the floor, I could partially stand behind her and get some traction.

I eased the swollen tip of my shaft up against her lubed hole, rubbed it around a little, and then pushed. There was no letting me in.

I tried once more, again without success.

I went back to using two and then three fingers to loosen her up, and then, while inserting the vibrator again, I applied more lube to her asshole and my condom covered cock.

After a few minutes, I tried again, telling her to push back against me.

I held onto my cock with both hands and pushed the tip directly into her opening.

No way; she was still shut tight. And this time she told me it hurt a little.

I applied additional lube, used my fingers and her vibrator again, massaged her ass cheeks, and then lubed up the handle on the hair brush.

The larger hairbrush handle slid easily into her ass. I moved it around and in and out for several minutes.

Again, I pushed the head of my shaft against her opening and pushed steadily and firmly forward, while she pushed back.

Gail suddenly let out a yelp; the head of my tool was in.

Immediately, she yelled, “Stop! Stop!”

She reached back with one arm and placed her hand on my chest, holding me back.

I waited patiently until she removed her hand and told me to continue, but to do so slowly.

She looked back at me, her face sweating, and it seemed, looking like she was in a little pain, and emphasized the word “slowly.” 

For fifteen minutes, with the help of more lubrication and Gail’s efforts, I gradually and slowly inched my cock into her hole, stretching it open, and stopping every once in a while so she could get used to its girth.

Finally, my manhood was buried deep in her, and I was able to slowly slide my full shaft in and out of her ass.

Soon, however, I realized that there was a problem with the condom. While my cock was sliding in and out of Gail’s ass, the condom stayed in place, buried deep in her hole.

Gail, of course, was focused on her first time with a cock in her ass and had no idea that there was a problem.

I slid my cock out of her ass and the condom. There was a moan of disappointment.

I pulled the condom out of her ass, squirted more lube on her asshole and on my cock, and slid my bare shaft into her ass.

To hell with the condom!

There we were, on the hotel room carpeted floor, Gail on her hands and knees, and me partially standing and partially kneeling above and behind her.

Now I could fuck her in the ass.

The preparation time had allowed me to gain some control over my own need to cum. Now I could continue for a few more minutes without fear of unwillingly spraying my sperm all over her ass.

I was in her ass, I was hard, and I was increasing the rhythm little by little.

Gail, as her anxiety dissipated, liked having a cock in her ass.

There were no words, and only a few moans and groans. But there were other wonderful sounds and noises coming from deep inside her, and they were un-mistakenly sounds of pleasure.

And then there was the look on her face. That wonderful look.

It was well worth the long effort.

Gail showed little sign of cuming. Yes, she let me know how good it felt. Yes, she did not want me to stop. Yes, she encouraged me to go faster and harder. Yes, she was making all of the right sounds and noises.

But if this was a race, I was going to lose and cum first. No question.

I pulled my cock out of her ass and flipped her onto her back. Once again she expressed disappointment, this time with a tinge of frustration.

Gail had never done this before. I’m sure she thought that I had given up on her ass.

She looked at me with a quizzical expression as I retrieved the vibrator and put it on the glass coffee table next to us.

I bent Gail’s legs back again, this time with her knees up by her ears, exposing her pussy and asshole, which was still wide open and waiting for me.

I put more lube on my cock and in her open hole and slid my hard muscle into her once again. She accepted my shaft eagerly and moaned as its full length slid into her.

There was a faster, harder pace and after several minutes, I directed her to rub her clit.

With both hands she furiously rubbed her swollen clit.

Now I could fuck her ass, look into her eyes, watch the expression on her face, and listen to the wonderful noises and sounds of pleasure she was making.

Her ass was tight, and milking my shaft. She was sweating and gasping for air, then holding her breath, and gasping for air again. A lip-twitching and twisted half-smile exposed her clenched teeth. Her eyes were half-shut and she had a look of pain mixed with pleasure, anxiety, expectation and need.

“God, don’t stop, don’t stop! Fuck my ass! Yes! Uuuunnnngghhh! Uuuuunnngghhh! Yesssssssss.”

Keeping my balance, I reached for the vibrator and tossed it on her stomach.

“Use this on your clit,” I said, now also out of breath.

She worked the vibrator furiously over her cunt.

Her breathing was fast and heavy. She grunted out words of pleasure, and continued to implore me to fuck her ass.

I stabbed her hole as fast and hard as I could. She begged me to go faster and harder.

Sweat ran from my forehead and dripped off my nose onto her stomach, where it streamed down to and pooled in the hollow of her navel.

I fought hard to control myself, but was quickly reaching the point of no return.

Gail went silent. Her head stretched back, her body arched up off the floor, and her mouth opened wide in a silent scream of pleasure.

Her pleasure was so intense that she froze in this position. Her stomach muscles rippled in rhythm. She began to shake and twitch, and she violently jammed the vibrator into her clit. She became engulfed in her climax.

“Oh God! Oh God!” she screamed over and over, gasping for breath.

Her body shook, twitched, and jerked violently as she buried the vibrator in her slit.

Her nose was running. Her lips trembled with an odd, curly smile. Her pussy ran freely with her juices. Tears streamed from the corners of her eyes down her cheeks, dripping onto the floor. Spittle ran from the corner of her mouth down to her chin.

“I’m cuming! I’m cuming!” she screamed.

For a wonderful minute, Gail experienced the most intense orgasm of her life.

I hung in there as best as I could, but I was done.

I pulled out of her ass, grabbed a fistful of hair, pulled her face up towards me, and stroked my cock furiously, aiming as best I could for Gail’s face. My head was going to explode with the pressure.

Then I received the wonderful release that my body craved.

Hot cum spewed out of me and I was overcome with the intensity of the pleasure.

I don’t know where my mind went at that moment. I had no awareness of what was around me. I was consumed with wave after wave of pleasure.

My legs gave way and I fell back into the end of the bed. I stumbled around, trying to get up, and falling back against the bed. Finally, I just sat at the end of the bed. Out of breath, sweating, exhausted, my cock twitching and leaking cum.

I became aware of Gail’s breathing and her little moans of pleasure and leaned over to her.

Not only had I cum on Gail’s face, but there were four lines of my load ranging from her hair, just above her forehead, down to her lips and chin, each line about an inch apart.

I reached for Gail and drew her body in next to me.

Cum was sliding down her face, over her cheeks, nose and lips. Gobs of cum dripped in long strings from her chin onto her breasts and the floor. As she continued to moan, little threads of cum stretched between her lips.

It was a sight that I would not forget.

Gail eventually went to shower. I stayed behind to clean up.

I grabbed the used condom and placed it in some tissue paper and threw it away.

Not only had I cum on Gail’s face, but apparently also on the glass coffee table. Two pools of ejaculate were on the glass top, with some dripping down off the glass edge onto the floor.

I used more tissue paper to clean up that mess, and made my way into the shower to join Gail.

It was 3:00 a.m. Sleep came easily.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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