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Anal Anywhere, Anytime Ch. 02

BEFORE CHARLOTTE

As long as Walt could remember he had been drawn to a shapely female bottom. I didn't have sex until I was 18 but I had hundreds of boners from just looking at the outline of curvy buttocks contained in skirts and slacks. I found myself watching TV hoping to get a look at an actress's derriere. Even during commercials, I checked out a curvy female bottom.

I liked watching women's volleyball with the players in their skimpy tight shorts. Figure skating was particularly appealing to me. I loved watching the toned skaters with their lovely legs skating backwards heading into a jump. The short skirt would usually flip up displaying the panty covered cheeks. Magazines and store flyers often had pretty women in lingerie I liked looking at the curvy bottoms.

It was in my senior year of high school when I had my first sex. I went out with a girl named Bonnie, also 18, who was known to have sex with other guys. She was not pretty but not bad to look at and she had an incredible body. The other guys raved about her tits but it was her ass that got my attention. Bonnie gave great head and she loved to get fucked. She had never done anal but had thought about it.

I was the first guy to pay so much attention to her ass that she wanted to go further. We kept going out and each time I would finger her bottom using hand lotion. One time, Bonnie brought a lubricant with her and she offered her ass to me. I was ecstatic and I almost came just from preparing her for my cock. My dick was a smidge short of seven inches and not too thick. That first time I wasn't in her ass five minutes before I came and flooded her rectum.

Bonnie liked the feel of the seed rushing into her channel. Before we had more sex, she used the bathroom to expunge the massive load. I seemed to stay hard all night and I fucked her ass three more times. Each time, Bonnie would douche her bottom before the next session. She liked anal sex but she made sure that I made her cum too. We experimented with different positions. My favorite was doggy style as I loved watching my cock slide in and out. Her favorite was the spoon position with my one hand fondling her breasts and the other fingering her pussy while I fucked her ass.

We continued to date and have sex as often as we could all summer before we went off to college. Once in college, I was always on the lookout for great looking asses. Over the four years I managed to find a number of girls who would do anal. I earned the reputation of being a butt fucker. A couple of the girls had talked me into giving them massages and I loved doing it. Of course, I would spend a lot of time on their shapely bottoms.

After I graduated from college, I joined an international marketing company and spent some time in Paris. I had four years of French in school and was nearly fluent. Even though the business language of Europe was English, I liked understanding French. In a short time, while in Paris, I became fluent and spoke French most of the time socially. I learned that many French women were fond of anal sex and I was in heaven.

On one occasion, I was hoodwinked buy a French ladyboy. Instead of being angry when I discovered the truth, I fucked the ladyboy's ass three times. The ladyboy had a lovely ass and from behind looked like a lovely young French woman. I learned on that occasion that I could fuck the shapely transgender ass of an attractive ladyboy. Although I didn't seek out ladyboy's, I did not shy away from them either.

I fucked the first gay ass in southern France. I spent a week's vacation on the Riviera and one day saw this absolute drop-dead gorgeous ass in a thong bikini. The problem was it belonged to a very handsome young Frenchman. The guy wore his hair long covering his ears and the nape of his neck. He looked more like a flat chested French woman than a guy. The guy's body was golden tan including his buns and I stared at the ass all day.

I walked to the water and purposely passed the guy lying on his belly. The scrumptious ass cheeks were perfect and rose above the rest of the body. I actually felt my cock stir from looking at the marvelous derriere. I knew that I could easily fuck that fantastic ass given the opportunity. That opportunity would present itself later that day.

For the remainder of the day, I kept checking out the French babes. Most of them topless and some completely nude. I had been informed that it was nearly impossible to pick up a chick on the nude beach. However, later in the evening at the clubs and lounges is where it happened. I was at a lounge after dinner when the guy with the great ass approached me.

We spoke French and got along. He told me that he knew that I liked his ass. Then he invited me back to his place. That night I fucked my first gay ass, not once but three times. I even spent the night and fucked the pretty Frenchman's ass, two more times in the morning. That day I felt a bit embarrassed and went to a different beach. A day later I returned to the nude beach but did not see the pretty gay. In fact, I only saw the gay on that one day.

I did manage to meet a couple of French women and enjoyed my time with them. I returned to Paris after my vacation and in another month, I was back home in the states. At the age of 26 now, I would work out of the home office. I had become more mature after my stay in Paris and I was also a changed man. I was still addicted to anal sex and I had learned that I could fucked ladyboys and gays with shapely asses just as easy as women.

BACK TO CHARLOTTE

It was a few weeks before Charlotte and I hooked up again and it was quite by accident. I had worked late one night and I stopped off at the pub for a night cap. It was a slow night and I was the only one in the bar until Charlotte came in. She had been out bar hopping and hadn't found anything to her liking so she decided to swing by the pub on the way home. She had not eaten dinner so I suggested that we grab a burger and a drink together.

Charlotte and I sat side by side at a bar table facing the bar. As we ate our burgers and sipped our beers, I ran my hands over Charlotte's nylon covered thighs. She was wearing pantyhose under her light blue mini dress but without panties. I slid my hand between her thighs and covered her hose protected pussy. I rubbed her cunt through the hose and her pussy got sopping wet. We finished our burgers and beers and then left the pub. When we got out to the parking lot I asked Charlotte if she wanted to sit in my car for a few minutes.

"You better believe it, as worked up as you got me in there you better take care of me tonight."

We got in the back seat of my two-door sports car and I immediately peeled off her panty hose. I lowered my pants and underwear to my knees and the two of us played with each other for several minutes. The car had louvered rear windows so it was impossible for anyone outside the car to see in the back seat. There was something very erotic about being partially clothed but still having access to each other. Charlotte had her legs spread wide as I fingered her pussy and pushed her cunt juice into her ass. She stroked my cock with her hand as I prepared her for another ass fuck.

I never knew anyone like Charlotte who could get so wet during foreplay. My hand was sopping wet and within minutes I had her puckered opening coated with her own pussy juice. I positioned her so that she was kneeling down on the back seat and I knelt behind her. I put my cock in her pussy and let it soak in her juices before I lined it up with her ass. Once again Charlotte reminded me.

"Not too deep at first and then deeper."

I eased my cock into her ass as she maneuvered her body to accommodate the anal penetration. She had her head down on the car seat turned to one side and I watched her face grimace slightly as my cock made its way into her ass. She moaned and groaned as I slowly fucked her going a little deeper in her ass with each thrust. Once I was all the way in, I picked up the pace and fucked her until I flooded her ass with my cum. Charlotte had her fingers buried in her twat and she brought herself off as I plowed her ass. When my hips stopped moving, she milked my cock with her sphincter muscle and then her hips gyrated as her own orgasm overtook her. I had to hold her tightly to keep my cock in her ass as her hips jerked out of control.

My cock softened and I eased it out of her ass. I knelt there looking at her dilated anus and watched as my semen trickled out of her rectum. Charlotte remained still for a few minutes with her dress thrown up over her back and her ass on display. I had some paper napkins in the car and she used them to wipe the semen from her bottom before she sat down on the car seat.

"You definitely have the largest cock that has ever been in my ass. Do you know how big it is?"

"Well Sharon measured it one time when she was blowing me and she said it was about 7 inches long and just over 5 inches around."

"It certainly felt bigger tonight."

Charlotte did not bother putting on her pantyhose when I pulled up my pants. I opened the car door and we got out of the back seat. She said that she was glad that she ran into me, then she said goodnight and made her way over to her car. I watched as she got in her car and as she did her skirt flew up and flashed her bare pussy. After she left the parking lot, I drove home in a very sated state.

The next time I ran into Charlotte at the pub she was with Hal and Georgia. The four of us drank and socialized for a while. I offered to take Charlotte home to her sister's place. It was pouring rain when we left the pub. I ran and got the car and picked her up at the door. I drove her to her sisters and it was a blinding rain. I pulled into the parking place and we waited for the rain to let up some. I decided it was time for more car sex.

"Charlotte, let's get in the back seat."

"It's raining out."

"Recline the seat, it will be easier to get in back."

She reclined the passenger seat and got on all fours to crawl in the back. I could not resist goosing her curvy ass under the short skirt. She giggled and got in back. I joined her. It was a repeat performance from the last time with me stripping off her pantyhose in the back seat of my car, lubricating her ass with her own juices and fucking her tight ass. It was exciting for me to strip off her hose and fondle her legs, pussy and ass. Charlotte seemed to like being without her panties and hose in the back seat of the car. I took my time with her, fingering her pussy and ass driving her crazy, until she finally begged me to fuck her in the ass.

I did what she asked and as I fucked her ass, I went a little deeper each time. Soon I was balls deep in her ass and I picked up the pace. My cock felt longer and thicker than I could remember at that moment. I reached around Charlotte with my left hand and played with her tits through the dress. Then I moved my right hand to her pussy and pushed three fingers into her cunt. Charlotte was going wild and she was creaming all over my fingers as I plowed her ass. My cock was throbbing in her and I felt my pending ejaculation building in my balls. One more deep thrust and I held my cock there as I exploded in her ass. My cock pulsated as streams of cum shot into her ass. Charlotte instinctively clenched and unclenched my cock. She milked every drop of cum from it.

I handed her the paper napkins to catch my seed and she wiped her bottom clean. The rain had let up some and it was a good time for her to head inside. I smiled as she picked up her pantyhose and carried them into the apartment. It had been another impromptu night of great anal sex in my car. I drove home feeling very sated.

FIRST TIME AT THE CONDO

Charlotte had stayed over on a Friday night and we had had wonderful sex. On Saturday morning it had been great again. After breakfast we relaxed with a second cup of coffee and read the morning paper. She was anxious to watch some anal porn but I convinced her to wait until after lunch. It was 2:00 PM when we settled in the living room to watch porn, I explained the videos I had to her.

"They all have oral sex in them but only part of the foreplay. I don't think you will like the ones with facials so I suggest this one. The guys always cum on the women's ass."

"I agree. I don't want to see guys shooting on the women's faces."

The movie I played had Italian porn stars, beautiful women and guys with big dicks. Every woman in the movie got fucked in the ass. A couple of scenes the guys would shoot on the buttocks aiming their release at the anus and then put their dicks back in the scrumptious ass. The scenes all started the same way with seduction. The guys would begin fondling the women eventually exposing breasts and vaginas. The guys would eat pussy and then the women would give head before they began fucking.

The pussies would be fucked in a number of positions; missionary, doggy-style and riding the cocks. The guys would then rim the women before putting their dicks in the hot asses. Even the anal sex was performed in various positions. I only liked watching the doggy-style and spoon positions. Charlotte agreed that she liked those positions the best. She also fast forwarded through the oral sex scenes as that was not her thing. She was intrigued by the guys cumming on the buttocks and putting their cocks back in the asses.

She was amazed at how beautiful the women were and how they handled the big dicks in their ass. We were curled up on the sofa in a spoon position. I fondled her breasts and diddled her pussy during the movie. My cock was stiff and pressed into her bottom. We were both hot before long and went back to my bedroom. Charlotte was anxious for me to fuck her pussy first. Then she wanted we to cum on her ass and put my cock back in after shooting.

Using her natural juices, I prepared her ass. I lined the head of my cock up with her anus and pushed it gently in. The sphincter opened easily and the head popped in. She put a hand back on my leg to slow the penetration and then she guided the action from that point. I continued to press forward each time adding another inch or half inch of cock into her ass. I eventually had the entire length in her ass.

I slowly fucked her with long slow deliberate strokes. My cock would almost leave her ass and then it would disappear as I pushed it all the way back in. Charlotte was breathing hard and I reached down to finger her pussy while I butt fucked her. Her hand was already buried in her pussy so I returned to massaging her shapely ass as I watched my cock slide in and out of her stretched puckered opening.

"When you are ready to cum take out your cock and aim it straight at my anus. Then after you shoot put it back in my ass and push your stuff in with it."

I fuck her hard as my hips slapped into her ass cheeks causing them to jiggle slightly. My cock was rock hard and I could feel the early buildup of another ejaculation. Charlotte was using her sphincter to squeeze my cock as it was imbedded in her ass. On the verge of cumming I pulled my cock from her ass and aimed it right at her dilated anus. My body tensed briefly and then I fired rounds of semen this time hitting her pucker as she had asked.

"Oh yeah that's it I feel it."

My seed bounced off her anus and most of it trickled down over her pussy lips. Some of it gathered around her anus and I pushed my cock back in her ass. As I penetrated her rectum again, I pushed a small amount of semen in with my cock. Charlotte then milked my cock dry with her sphincter muscle draining every drop from my pecker. My cock slipped from her ass and I watched as she squeezed the little bit of cum out of her ass. Charlotte rolled over on her back and I flopped down beside her. We were both sexually sated so we just lay quietly together for several minutes before Charlotte finally spoke.

"That was a bit kinky for me. I like it better when you cum in my ass."

"I do too, although it was somewhat erotic watching my cock shoot on you."

"I like the feeling of you cumming in my ass. I wish we could use the jacuzzi."

"We can, it's only a light rain and there is a roof over the jacuzzi. You brought your swimsuit, right?"

"Yes, I remembered it."

"Let's put on our swim wear. I'll give you one of my sweatshirts to wear."

We got ready to go to the jacuzzi and I admired Charlotte's shapely legs below the sweatshirt. She looked very sexy with the sweatshirt just covering her bikini clad bottom. I grabbed some towels and we walked in the light drizzle to the hot tub. It was a bit chilly but the water soon warmed us up. At first, we relaxed sitting apart from each other but then I got frisky with her.

I had Charlotte sit in front of me and I sneaked my hands into her bikini top and bottom. Her nipples hardened immediately and her pussy, as always, was sopping wet. I left her tits momentarily and freed my cock through the leg opening in my Speedo. She cooed with desire but remained passive. I turned her to face me so that she could sit on my dick.

"We're not really going to do anything here are we?"

"Sure, why not have some fun?"

"Someone may come down here."

"Unlikely in this weather but I can keep an eye out."

I moved her bikini bottom to the side giving me access to her pussy. Guiding her onto my lap, my cock eased into her pussy. Charlotte slowly settled onto my cock and buried her face in my shoulder. I grasped her buttocks and she began to ride my cock.

"Oh my God, I cannot believe we are doing this outdoors."

"This is wild, isn't it?"

"Are you able to cum again?"

"Probably not but I bet you will."

"You better believe it. God your cock feels good in me."

I saw the look on her face and I knew she was close to an orgasm. She stopped moving and then I thrust into her. Charlotte buried her face in my neck and shoulder to muffle her cries as if someone would hear. Her body trembled and I held her tight as she made three quick thrusts with her hips and then stiffened. We stayed coupled together for nearly a minute before she lifted her head and sighed.

"Oh wow, that was something. I came hard."

"Yes, you did. Are you okay?"

"Yeas, I'm fine but that was intense. I think it was the excitement of being outdoors in a public place. Did you cum?"

"No, I can wait until tonight."

Charlotte moved off of me and we straightened our swimwear. She rested her head and closed her eyes, savoring the feel of the warm bubbly water. We stayed in the hot tub for another ten minutes before returning to my condo. The rain had picked up a bit so we put the towels over our head and hustled back. Once inside, I put the towels and swim wear in the wash. We showered and dressed in shorts and tees. I got drinks for us and we relaxed in the living room on the sofa. We talked about the porn video and other topics came up.

"I liked most of that video. It seems there always has to be a lesbian scene."

"Did you ever make it with another woman?"

"When I was in the Army, a couple of us fooled around. It was strictly sex and making each other cum. What about you? Ever do anything with another guy?"

"Kind of, it was with a ladyboy."

"A what?"

"Ladyboy, a transgender person."

"Oh my God, I've heard of them but have never seen one."

"This was in France and you would not have known by sight. The ladyboy was absolutely beautiful. I thought that I was with a pretty young woman until we undressed."

"You had sex then?"

"Yes, I fucked her ass three times that evening and then two more times in the morning. From behind it was just like anal sex with a young woman."

I had decided not to mention the gay guy in the south of France.

"Describe this person, this ladyboy."

"She wanted to be referred to as a she. So, she had long silky hair, lovely legs, small pert breasts, a very nice derriere and a small penis. From behind she looked as desirable as a woman. I have another video that has a threesome scene that includes a very attractive ladyboy."
"Oh, we have to watch that one."

"Okay, we will, after dinner."

MORE PORN FOR CHARLOTTE

After dinner and a few glasses of wine, Charlotte was anxious to see the porn video. She only wanted to watch the scene with the ladyboy. I put the Italian made video in the player and we sat on the sofa. Charlotte curled up and rested her head on a throw pillow on my thigh. I fast forwarded to the threesome scene.

In the video, a couple meets an attractive woman in a hotel cocktail lounge. They chat briefly and invite her to their room. The porn actress and ladyboy are both gorgeous. I sense that Charlotte is anxious to learn which one is the ladyboy. The three enter the hotel room and the guy sits in a chair and watches as the others move to the bed. Both are wearing black evening gowns with thigh high hose.

The guy watches as they kiss and then his partner makes her descent. The scene is well done and it looks like the woman will soon be eating pussy. She lifts the skirt and pulls the panties to the side, only to discover a soft penis. Undeterred she takes the cock in her mouth and sucks it into hardness. The ladyboy's dick is about 5" when erect. The guy gets undressed and approaches the bed with his impressive cock and the ladyboy takes it in her mouth.

As the scene plays out everyone is soon naked and they have sex in a variety of positions. It begins with oral, the guy eating pussy while the ladyboy sucks his cock and the woman sucking the ladyboy dick. The next scene has the woman getting fucked while she sucks the ladyboy. Then the ladyboy fucks the woman in the ass while she sucks the guy. Another segment has the guy fucking the ladyboy in the ass while the woman sucks the ladyboy's cock.

The final position is with the woman being double penetrated. The guy is underneath in her pussy and the ladyboy in her ass. The ladyboy is the first to cum. She pulls out and shoots a large load on the woman's beautiful ass. Next the guy pulls out and shoots his seed up between the woman's legs onto her buttocks. Some semen hits the ladyboy's cock and testicles. The camera pans out showing the cum-covered ass and two cocks resting against the buttocks. I paused the video.

"So, what do you think?"

"That was incredible. I have never seen anything like it. That ladyboy was drop-dead gorgeous. Who would have known that she had a cock?"

"I agree, it is scary."

"Can we watch it again?"

"Sure, let me get another drink for us."

Charlotte raised her head so that I could get off the sofa. I refreshed our drinks as she rewound the video. This time she sat up with her legs curled under her next to me. We watched the same scene as we enjoyed our cocktails. When it was over, Charlotte commented on it.

"Those porn actors were excellent. I loved the discovery part when she learns that the other woman has a cock."

"The actress is a popular Italian porn star and she appears in a lot of videos. It is amazing that someone that beautiful does it all on the screen."

"I'm ready for bed."

"I'm ready for your ass."

We went to bed and within minutes, I was in Charlotte's ass. She wanted to spoon so we were on our sides. It was the routine that she loved with me fondling her breasts and fingering her pussy while my cock was in her ass. That night I came in her ass and we stayed in the spoon position. My cock softened and slipped out but we remained on our sides. We fell asleep quickly and slept soundly.

The next day, we followed our ritual of morning sex. Afterward, we showered, dressed and went out for breakfast. Following our leisurely meal, I took Charlotte back to her sister's place. That afternoon I relaxed watching golf on TV. It had been a fantastic weekend with great sex.

AFTER CHARLOTTE

I had been seeing other women during the time spent with Charlotte. Two of them, Andrea and Pamela were into occasional anal. There was also my 38-year-old neighbor Jackie, an insatiable redhead who loved anal sex. About a year later I survived a corporate downsizing but Charlotte did not. Eventually she moved away and I didn't see her again.

I continued to date Andrea and Pamela. I thought that I would miss Charlotte but Jackie solved that problem. She had the roundest, shapeliest ass I ever fucked and I could not get enough of it. In turn she could not get enough of my cock. Since we were neighbors, it was very convenient and much of our sex was impromptu. Jackie would call me and tell me that she was thinking about my cock. My reply was that I was thinking about her ass.

More about Jackie if there is a third chapter.
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