Chapter 1

Sometimes it amazes me the situations I get myself in. I am standing here with a tube in my ass and a beautiful woman administering my first enema, and for what? Well for the need to have anal sex of course. I can't think of any other reason to subject myself to this humiliation. My desires for the ultimate in intercourse with any woman have given me a few slaps on the face and a lot of hard feelings.

Growing up in the late eighties, watching a fare share of porn movies has made me believe that all women want and need to be fucked in the ass. I thought that all young girls were taught the phrase "Please jump on me and ram your cock deep in my waiting ass!" I have ventured on my quest to no avail. My days have been spent thinking of the ultimate situation to be in, lying on my back my cock deep in a lovely woman's ass.

During high school I had more than my fair share of pussy, but the quality was never there. Finger banging Betty Joe after the high school football game was not my idea of quality. Sometimes I wish I could find a woman that enjoyed having sex, not the idea of having sex. Entering college seemed to be the solution to the problem, but college girls are not much different than high school girls.

Because of all my past disappointments I am reluctant in making the first move towards my venture. That is why I cannot believe that I am here stroking my cock in preparation for the Holy Grail. It seems to me that I am getting ahead of myself. This event really started some time ago.

It has been two weeks since Denise dumped with me and I am feeling very depressed. I wonder why I feel this way because it is not like she was any good in bed, or even that great looking. It is probably the fact that I am sitting alone at the local drive in with a beer in one hand and rubbing my crotch with the other. At least if I was with Denise I would be pounding her from behind so I didn't have to look at her face.

Knowing that you are alone gives yourself greater freedom than knowing you are with someone. Yes, it is a public place but you do not have to worry that you are going to embarrass your lady friend. Slowly I unzip my pants and slip my hand under my underwear grasping my cock. As I take another swig of my beer, a young lady walks between the car parked on my left and I. Suddenly the fact that I was in public sunk deep in my heart.

Not knowing if she saw what I was doing gave me a little feeling of horror. It would be hard to live down the reputation of being caught masturbating in public. I did not know who she was so I watched closely where she was going. After she disappeared behind the building I suddenly heard a group of girls laughing. The fact that I was an object of so much laughter was worse than any deviant reputation. But maybe they were not laughing at me?

I figured the young woman was partying with the large group of girls gathered on the other side. Maybe it was just the drunken stupor that they were in that gave them the giggles. I saw them as I entered the burger joint and it looked like they all had a lot to drink and were getting a little rowdy. There were a few girls that I knew from high school a couple of years ago, but I have not seen them in a long time.

Once I felt like the coast was clear I resumed stroking my cock thinking of being with a woman. Any woman would due for this fantasy because all I want to do was drink, ejaculate, and go home alone to sleep. This day seems like it will never end.

Just then I heard a knock on the passenger window of my car. All of a sudden the fact that I am stroking my cock in public came back with a fury. Too ashamed to look up I slowly pulled my hand from the elastic confines and zipped my pants.

"James, are you okay? Hey James open the door."

The voice sounded familiar so I lifted my chin to see who caught me in the most private of moments. To my surprise it was Jenn from school and she was smiling without any sign of disgust on her face. Relieved I unlock the door and let her in. Still a little embarrassed I was silent waiting for here to let me off the hook.

"Sorry to bug you, but my friend Lisa said that you looked a little down over here. I heard about Denise and I am sorry."

"Oh, its okay" I said shyly, "Would you like to sit down?"

"Yes, but for just a second I have to drive a few people home because I have had the least amount to drink."

"Maybe you should go and tend to your friends. I will be okay here by myself"

"It doesn't look like you are okay," she said looking straight into my eyes. I found it hard to make eye contact knowing she has seen me jacking off. "I'll tell you what, Let me take my friends home and I will come back and keep you company and we can talk."

"That would be nice Jennifer, but I do not want to be a bother to you." "You are no bother, I too can feel a little lonely from time to time. And please call me Jenn."

"Okay Jenn I will wait for you here, if you change your mind I will understand."

Jenn reached over and grasped the hand I moments ago had tightly rapped around my cock. "I promise you I will be back, give me twenty minutes and we will talk." Did she just wink? She couldn't have. I must of just wished it and my imagination did the rest. Quickly she stepped out of my car and jogged behind the building. For the first time I noticed what a nicely shaped ass Jennifer has, or is it Jenn.

Jenn and I have really not had any meaningful conversation in the past even though I had at least 3 classes with here in high school. I was always hanging around with the Jocks and she was more the country version of the educational elite. A pretty girl with a great smile, but she was not the one to wear revealing cloths or any thing tight enough to show off her curves.

Tonight though, she was wearing a pair of very tight jeans and the most revealing pink halter-top made of cotton. Tonight was a little chilly so I envisioned the sight of her little pink nipples rising in the crisp air. I felt the blood rushing back to my waist after the embarrassing deflation I felt a few moments ago.

In high school, Jenn was the type of girl that had rumors of sexual exploits spoken of her but I have never met a guy with first hand knowledge of her desires. She was never dressed like a slut always wearing clothing that was comfortable but always baggy. Generally she was kind of an outcast not quite fitting in with the 'a' students because of her reputation. Didn't bother her though, because she graduated within the top three people in her class continuing her schooling at college with a full ride scholarship.

With the image of perk nipples brushing against the thin cotton top, my hand stroked even harder towards my goal. The idea of not being alone anymore made my attitude brighten but a sense of urgency crept up on me wanting to cum before my rendezvous with a very pretty straight 'A' student. Pumping with all of my might turned my cock head deep purple, feeling like the reward was near.

Suddenly the passenger door opened with great speed, inspiring me to jump to cover my actions.

"Hey wait a minute, don't do that by yourself. Let me help you with that," said Jenn. Relieved I slowly returned to my position while she helped herself to the seat next to me. "Why don't we move your car over there where it is not so bright so I can help you finish."

Trying to hide my excitement I started my car and quickly moved it to the furthest parking space from the building and the glaring lights. Once the ignition was turned off, Jenn briskly reached for my prick while pressing her lips against my waiting mouth catching a small amount of her sandy brown hair between our lips. Just as her tongue reached the inner recesses of my mouth she pulled back leaving her hand around my cock.

"I had to break the ice somehow," she said with an arousing smile. "Now will you tell me why you are all alone on a Saturday night?"

"Well as you know Denise broke up with me, and I have just felt like being by myself. You don't have to rub my dick if you don't want to."

"But I want to and stop feeling sorry for yourself. Denise was just a woman with the head that looked like a horse and a body from a 12 year old girl." Jenn was taken back with the words that she blurted out without thinking. "Oh, I'm sorry I didn't mean to say that I know that you liked her a lot."

"It's okay," I said with a sigh of pain.

"Can I ask you what you saw in that woman anyway? Was she a great lay or what?" Her hand kept stroking during our conversation like nothing was happening.

" No. She was about the worse I have had in bed, I think that it was just the fact that I was not alone. I was with someone."

"I figured she was bad in bed. A woman with tits that small does not have the equipment to satisfy any man." With that spoken she casually lowered her top with her free hand rubbing across her left nipple.

The sight brought me to an instant climax cumming all over the steering wheel in my car. Jenn smiled seductively and with one graceful motion she released my cock and grabbed the steering wheel.

"Do you mind if I drive?" Instantaneously she leaned over and licked a large glob of sperm off the wheel. With my juice coating her tongue she leaned back and lifted her top uncovering her rather large chest and rosy erect nipples. Her breasts were defiantly large enough to fill a large D cup bra, but she was not wearing one.

"I have an instant cure for your situation. Here is my address' handing me a business card 'pick me up tomorrow night at 6:30 and lets go have some fun."

Without a single word from my bewildered face she exited my car into the cool night air pulling her top over her beautiful titties. Once the door slammed shut I looked down at the card handed to me and saw her name and address surrounded by little pink hearts.

"Hey James. Roll down your window."

As I rolled down my window I noticed her nipples stretching against the fabric wishing I had enough nerve to reach out and grasp one.

"By the way, wear some shorts and a tee shirt but leave those ugly boxer shorts at home." With the end of the statement she walked away. Watching here for at least 15 seconds in my rearview mirror, I was entranced by her attitude and the sultry way her ass swayed from side to side. It was almost like she was trying to entice me with the curvature of her hips.

Now I can't wait to go to sleep so tomorrow will come sooner. I felt like a small child wanting Santa to come sooner so he could play with all his newfound toys.

After a restless night of sleep I awoke to an awful thought. What if it was just a dream? Looking down seeing the cum stains on my boxers relieved my worries about the previous nights activities. Excited about the night to come I quickly cleaned my apartment hoping she would like to see where I live. It was amazing that I was so delirious about a woman that hardly knew I existed just 12 hours ago. Denise was not even a nightmare anymore because of the anticipation of wild sex with Jenn later.

Thankfully 6:00 came quickly so I dressed in a nice pair of jogging shorts and my favorite tee shirt for an unexpected evening. We lived in a small town so it was just a short drive to her house. Once I knocked on her door I was already showing an erection through my shorts.

"Come on in and make yourself at home" someone shouted from the up stairs window. Wait a minute that didn't sound like Jenn! Did I get the right house? Cautiously I opened the door to a well-lit room with a couch, love seat, and an armless chair. Upon closing the door I saw Jenn coming down the stairs.

What a beauty, she was not a supermodel by far; she was more like the farm girl next door. She was wearing a skimpy pair of silk shorts and a cut off shirt that hung just below her rather large tits. She was carrying a thin piece of fabric in her right hand grasping the handrail with her left hand.

"I have something for you to wear under your shorts when we go out."

"What?" I said in shock. "I thought we were going to stay in tonight?"

"That is a little forward for even you James. It is a little brisk out side but not uncomfortable so I thought we would have some fun. Your can change either in the middle of the room or you can use the downstairs rest room. So which is it?" handing me the thin piece of fabric. To my surprise it was a skimpy red thong made of silk. The fabric looked slightly used but that was not my concern at this time.

"Thanks, but I think I will use the bath room." As I walked towards the bathroom Jenn leaned over and whispered in my ear. "By the way I like forward men."

Shutting the door behind me I quickly pealed off my shorts and looked puzzled at the entanglement of underwear before me. For such a small piece of clothing it amazes me that it is so hard to put on. The thong was a little tight and the thin piece of fabric between my legs was pulled tight between my ass cheeks. Once I figured it out I put my shorts back on and exited the bathroom.

"It's a little better, but I think your excitement is showing" Jenn said. Looking down I saw the outline of my hard cock under my shorts. " Don't worry, I will take care of it later. Let's go. I want to have fun," she said with a sparkling smile.

Once in the car I start the engine and put in my Favorite CD.

"Okay, where to?"

"Well I think that I would like to play some miniature golf. It is a wide open public place so I don't have to worry about you jerking off."

With a chuckle I drive off. On the way we had a nice conversation with Jenn but she never once reached for my cock. I found out that during high school she was not so carefree because she was busy with her studies. Her parents made a deal with her that if she got a scholarship they would set her up in an apartment free of charge.

"That was the only thing I wanted," she said honestly "I am not very good at working.

"So who was that in you apartment earlier?"

"That was Cathy. She is my best friend. In exchange for some rent money she stays with me and keeps me company."

Was that another wink? My mind is totally out of control. Luckily we arrive and enter the Fun Park. Once I paid for admission we decided to play just the first 18 holes.

Jenn turned to me and tilted her head.

"Let's make a deal, if you win you get to do with me what you will. But is I win you get to go home alone to jerk off on your couch." She reached down and grabbed my balls and gave them a little squeeze.

Of course I am going to try my best. One the first hole it was very evident that she was not very good at the game. She sunk her ball in 7 strokes on a par 3 hole. Counting my blessings I sunk the ball in 2 strokes. Knowing that I am going to have the night of my life I continue on the next hole.

Before I took my first stroke, she motioned me to come to her.

"I forgot to tell you that I am not wearing any panties... The thong your wearing is the same thong I wore all morning.

Instantly I sprang back in shock moving to the second tee. As I looked down to line up my shot I saw the bulge starting to form in my shorts. Swing... Miss! All of a sudden the playing field evened up with my mind on what has to be the sight of her pussy under her tight silk shorts. All I could think of is ' is it bare or trimmed. Does she have a small clit or a more robust one?'

Well her plan worked, after 15 holes I was only up by 1 stroke. I had to have her. It is time for me to concentrate and the game.

"Is it my shot," she said with her index finger hanging out of her mouth. Reaching down she placed her ball on the tee making sure I saw her silk shorts riding up the crack of her ass.

Is it my imagination or is she getting better at this game? Or, was she just toying with me all this time? After 17 Holes we are now even and she is playing like the local pro. Just then a worker walked by.

"Hey Jenn," he said while keeping his eye on her and not watching where he was walking almost knocking over the large fiberglass elephant.

"Who was that?" I said.

"Well I forgot to tell you that I come here a lot and everyone knows my name. It's like cheers on TV but this is real life."

Now I am worried. I want this to happen more than anything. If she wins this hole all I have to look forward to is Rosie and her five sisters. Two can play at this game. As she lined up for her shot I stood right behind her. When she was about to swing I said so everyone could hear...

"I would like to lick your pussy for hours!"

Her shot went in the air right through the club house window.

"Looks like I win by default!" I said with great joy.

As she turned to me she said, "you know I am going to hold you to that! Let's get out of here."

In the car we decided to get some beer and go back to her place. As we drove up I noticed her house was dark except the light blue glow of a TV in an upstairs window.

"Cathy must be in bed already"

"Don't worry" Jenn said " we wont bother her and she wont walk in on us. We try to stay out of each others way when we have guests over."

Jenn unlocked the front door letting me in carrying the beer and locking it behind us.

"Why don't you sit on the couch and make yourself comfortable."

I walked to the couch turned around and sat down placing the beer on the side table. When I looked up I saw Jenn next to the door completely naked. What a beautiful sight! She was 5' 10" tall with very curvaceous hips. Her light brown shoulder length hair was fanned out behind her head lightly touching her tanned skin. Jenn was holding her light blue silk shorts in her right hand swinging them in the air.

"Are you sure you are ready for tonight?" She said with a grin. "From what you tell me, you are out of shape because you haven't had a real woman for a while!"

Slowly she sultered over to the couch where I was sitting lifting one leg and placed her foot on the back of the couch on my left side. With her right hand she eagerly parted her pussy lips and with her other hand she rubbed her breasts.

"Remember, you promised," she said in her best school girl voice.

Without delay, I leaned forward grasping her hips bringing her pussy to my face. The sent was amazing. Lightly perfumed and neatly trimmed her cunt was open to the advances of my lips and tongue. Slowly starting from the bottom I licked the open hole. Once I reached her clit I flicked it with my tongue. She arched her back moaning with desire.

Continuing to lick her clit I raised my hand and rubbed her pussy with my fingertips. Her juices started to appear from the delicate folds between her legs. She removed her hand so I could have more room to stimulate her crotch. Once my fingers were wet I slowly inserted one finger into her pussy twisting all the way. No words came from her mouth just moans of passion.

Her legs became to soft to hold her weight so I lifted her on the couch with my head planted between her legs. My pace became quicker licking the honey I have found as fast as I could. By now I have placed 3 fingers in her pussy plunging them deep inside her.

"Oh, yes! Finger my cunt harder! Please give me more!"

I removed my three fingers from her tunnel reaching to her open mouth placing them on her tongue for a sip of her juices.

"Suck on my fingers and get them slick with your spit. I am going to try four!"

She vigorously coated my fingers with saliva tasting her natural lubrication from my strong fingers. Without any hesitation I removed my fingers from her mouth and placed them next to the entrance to her cunt. With the two outer fingers I slowly parted her pussy lips forcing two fingers deep inside. Pulling out I found that She was very slick and waiting. Returning inside with 3 fingers she moaned with her hand urging me on forward.

This time when my hand retreated I rubbed my hand on the out side of her pussy smearing the juices on my finger. This time when I push in I took four fingers and held the tightly together. Slowly they passed the outer folds seeking the inner warmth. Once to the second knuckle I paused to check on Jenn. She then lifted her legs high grabbing the couch on both sides.

I continued pushing in until my fingers were inserted to the palm. A wave of pleasure worked over Jenn bucking her hips into the air.

"Please fuck me hard with your hand! Please!"

With that request I started pumping my hand pushing hard on her cervix. Within a couple of minutes Jenn froze and I thought she was hurting so I started to pull out when she grabbed my hand and forced it all the way back in. I could feel her muscles contracting to the point of pressure against my fingers.

"I'm cumming... Push hard on my pussy..."

With all of my might I pressed on her tight cunt. After a while she relaxed her muscles and I slowly withdrew.

"I want you now," she said between deep breaths.

Quickly I discarded my clothing freeing my rock hard cock from the confines of Jenn's thong. In one fluid motion I sank my cock into her wet pussy. I figured she would feel real loose after taking four of my fingers deep inside, but I found that her cunt was tight squeezing my cock. I rapidly forced my dick in and out banging her as hard as I could.

"Come on, give it to me. I want to feel you cock deep inside me" she said in a rather loud voice. By this time I was wondering if Cathy was listening to us carrying on. It would be fun if she would come and join us.

I turned Jenn over and raised her to her knees so I could pound her hard from behind. Inserting myself was not hard because she was so slick with own cum. This is, by far, the best position for giving her the deep penetration she needs. Pounding her was beginning to look like a couple of wild animals filled with pure lust.

During on of my moments of rest I pulled my cock out of her pussy repositioning it over her ass beginning to slowly push it in. Suddenly Jenn reached back and removed my dick and placed it back into her cunt. Figuring that I was denied once again I starting pumping as hard as I could. This time with even greater ferocity because the denial of my dream.

"I'm going to fuck you hard whether you like it or not" I yelled in anger.

It only took a minute before I was filling her hole with sticky cum. Small amounts of cum spilled out between her pussy and my cock buried deep inside. Quickly I came back to my senses feeling bad for my outburst. We both collapsed on the couch with my prick still inside her.

"Thank you for being rough with me. I really like it rough," she said panting heavily. "Would you mind if I got up and have some of our beer?"

"Of course not. Can I have one also? I feel so dry."

Jenn managed to spin to a sitting position pulling my cock out of her with a loud slurping sound. Reaching for a beer I could her see her large beautiful breasts hanging from her chest, what a beautiful sight. She picked out a drink and sat back before opening it up. She took a sip and handed it to me.

"You really wanted to fuck my ass, didn't you?" she asked.

"Did it show that much?"

"Yea, but I didn't mind I like it hard. I'll tell you what, you recover from tonight and next week I will you give you a lesson on what anal sex is all about."

I didn't quite understand what she meant, but I knew I would be getting a chance to fulfill a long lost desire I had.

"So you want to see me next weekend?" I asked knowing the answer.

"Of course. I have to get some rest tonight, but why don't you call me on Friday and I will let you in on the plans. Take my panties you wore as a remind you of the scent of my pussy."

With everything said I got dressed and gave her a short kiss good night and went home. The ride was short but mind could not grasp the pleasure I had tonight and the pleasure I might have next weekend.

The following week went by slower than normal thinking of Jenn and her openness to sex. What did she mean about my lesson? I guess I will find out sooner or later. Now that Friday is here I want to learn what is in store for me later. Picking up the phone I started to get excited just thinking of her. I started to get erect dialing Jenn's phone number.

"Hello" Jenn sounded a little hoarse.

"Hey Jenn, its James. Are you okay?"

"I'm fine. Just feels like I am getting a cold, but otherwise I am okay."

"Do you want to cancel our plans?" I said sounding deflated.

"No, I think I can manage. I hardly turn down sex."

"So what do you want to do this weekend?"

"Well I thought that I would cook you a nice dinner and have plenty of play time afterward. So how about 5:00 on Saturday, at my house?"

"Sounds great, I will be thinking of you."

"I bet you will, just remember what my ass looked like sticking straight in the air. And remember no underwear and wear shorts and a tee shirt. Bye."

And then the dial tone. I ran off to the bathroom to jerk off as soon as I dropped the phone to the floor. My imagination works overtime and the memory of her was too much. I decided that Saturday morning I would have to masturbate so that I could relieve some pressure for the night to come.

Saturday evening came quickly, thank god. Dressing for the occasion was simple. I have lots of shorts and it saves me time not picking out the right pair of boxers. I wondered what she would have for me to wear when I got there? On the corner of my dresser I see her used thong. Picking it up and bringing it to my nose brought back a flood of memories. The scent seemed almost sweet not bitter like I expected.

The closer I got to her house, the harder my cock got. I realized I had to play my cards right or I might go home alone with cock in hand. Arriving at her house was uneventful, to say the least. I knocked on her door trying to contain my enthusiasm.

"Hello?" the door opened suddenly.

"You must be Cathy." I said looking over the tall blonde standing at the door. "Is Jenn here?"

"Yes she is, come in we have been waiting for you."

I followed the blonde in noticing that she was wearing a short white lab coat with stockings and heals. She had just about the best ass I have ever seen. It was large by some people's standards, but I loved it. It was tight and flowed with her every movement. When she reached the dining room she turned around and I saw that she was not endowed with large breasts, just a little larger than average. That was okay, she made up for it with a great backside.

My attention was turned to Jenn, which looked pretty awful. She was wearing sweats and carrying a tissue or two.

"Glad you made it," Jenn said. "I'm not feeling great so I asked Cathy to help us with tonight's plans. I hope you don't mind?"

"No, but did you tell her everything?"

Cathy spoke up "of course she did. Not to mention I couldn't help but overhear your escapades last weekend."

A little ashamed I figured in some way she got off on listening to Jenn and I fucking on the couch.

"I thought we would have some dinner and the three of us could talk about our wants and fears."

"Fears" I said confused.

"Why yes," Jenn said "Don't you fear what we might do to you tonight"

'No, I have a pretty open mind about sex."

"Good, lets sit and eat. I may be sick but I still have my appetite."

We all sat down to eat and I was in a state of pure ecstasy. I felt like a kid in a candy store. Two beautiful girls and just me to satisfy they're needs.

Jenn started "Here are the rules. Tonight we are going to show you the time of your life and give you a little education in the process. Tonight we are going to show you the right way to enjoy anal sex."

Her words made me squirm a bit, but I still listened carefully to receive my reward.

"First, you are here with me." Jenn said with a hit of jealousy. "You are not to entertain your self with Cathy. If she touches you it is my insisting. You are not to make advances on her without my permission."

"Second," Jenn said looking straight in my eyes "if I say stop that is what you do. Okay?"

"Okay, I promise to be gentle."

"That's not what I said is it? I don't always like it gentle."

"That was not hard was it?" Jenn said matter of factually. "Are you sure you want to continue?"

"What's for dinner ladies."

Dinner was great. I devoured my chicken and had a very stimulating conversation with these two women. From time to time our legs would brush under the table which heightened the excitement of the evening. Once we were through I sat back to let my dinner digest.

"Why don't you go to the bathroom and wash up and Cathy and I will pour us some wine and move into the living room. When you are in there, you will find something for you to wear. We expect you to change and be out here in fifteen minutes."

Doing what I was told I got up and went to the little bathroom on the first floor. Once inside I noticed the only thing in there to wear was what looked like a hospital gown. Closing the door gave me a sense of privacy which I figured I would not have once I changed and went back out.