01.27.2015
To the Shameless,

Another story from work for your reading pleasure, but first the disclaimer. This story is mostly true. I have embellished it a little bit to make it a little naughtier but this is true at its core. Enjoy!!!!

I was 18 years old during the summer of 2004. I was supposed to go into the Air Force right out of high school but I chickened out at the last minute and ended up spending the summer getting high, getting drunk and getting laid.

This particular instance that I am going to tell you about is something that I am not particularly proud of but it was still damn sexy. I’m going to tell you the story of how I ended up having sex with a married woman.

It all started around July or August of 2004. As I said I was 18 and bored out of my mind so I was aimlessly driving up and down the back roads of the small county that I lived in.

“What to do, what to do?” I kept asking myself as I shifted gears in my old Toyota pickup when suddenly I felt my cellphone buzz. It was a text message from my friend’s wife Sara. She wanted to know what I was doing. I told her “nothing” and she replied back that maybe I should come over so the two of us could hang out. I texted her back “ok” and I headed that way.

It was about a five minute drive to her trailer from where I was so it wasn’t long after she texted me that I was there. When I pulled up I thought to myself how glad I was that she didn’t live in a trailer park. I could only imagine the shitstorm that would accompany all of the nosy neighbors watching me pull up to her house while her husband wasn’t home. Thankfully though, Sara lived in the middle of nowhere, and her only neighbor was her best friend Tiffany and there was still a good bit of space between their trailers.

I got out of my truck and I walked up to the door and knocked. I waited about thirty seconds and I knocked again but there was no answer. I knocked a third time and again, still nothing.

“John, is that you?” I heard Sara’s voice coming from the backyard.

“Yeah, it’s me! What are you doing?”

“I’m tanning. Give me a sec and I will come around,” she yelled.

“Well, why don’t I just come back there?”

“You can’t! I’m naked!”

Oh, I said to myself. Why is she sunbathing naked? She knew that I would be here in less than ten minutes.”

The thought disappeared from my mind when Sara opened the door. She was clad only in a towel and there was an apologetic look on her face.

“Sorry about that. I must’ve dozed off after I texted you.”

“That’s ok,” I said, doing my best to keep my eyes from the very deep cleavage that her beach towel was barely covering.

There was a brief pause and the two of us just sort of looked at each other.

“Do you want to come in? It’s hot as fuck out here and I doubt that you want to strip and tan naked with me in the back.” She chuckled loudly and I stepped into the trailer. If only she were serious, I thought to myself.

The inside of her home was decent. Sara kept it as clean as she could but with two kids running around it wasn’t always easy. She told me to have a seat and asked if I wanted anything to drink. I told her that I wouldn’t mind a beer if she had one and she went to the fridge and pulled out a Miller Light for me.

“Thanks,” I said.

“No problem.”

“So where are the kids,” I asked after taking a pull from my beer.

“They are with their grandparents thank God! I needed a break and they were nice enough to offer so I took advantage.” She too had pulled out a beer and took a long sip of the cool liquid.

“So what have you been up to,” Sara asked me, tugging at her towel to try and keep it up but she wasn’t very successful.

“Meh, not much. Just looking for something to do. What about you?” I finished the last sip of beer and I put it on the coffee table.

“About the same. Enjoying my alone time; getting a little sun. Do you want another beer?”

“Might as well,” I said and she popped another top for me. I took yet another long sip.

“So, where is Bill? Working?”

Sara face turned sour at the mention of her husband’s name. She looked as if it pained her to hear his name. I wanted to ask what was wrong but I felt that it wasn’t quite my place. Sara and I were friends but we weren’t really close on an emotional level.

“He’s out of town yet again,” she grumbled disgustedly.

“Oh,” I said nervously. “On business?”

“I don’t know and I don’t really give a fuck!”

I put the bottle to my lips and drank as much of the beer as I possibly could. “Maybe I shouldn’t have come over,” I said to myself as I put the second empty bottle down onto the coffee table. She saw that I looked uncomfortable and she went to the fridge to grab a third beer for me and another for herself. She plopped down on the couch next to me and told me that she wasn’t going to bore or bother me with shit involving her soon to be ex-husband.

“So,” I said nervously, “how was your tanning?” She looked at my eyes and saw that they were focused on her nearly naked body.

“Oh shit John, I’m sorry. I forgot to put on some clothes.”

She quickly got up and walked into her bedroom and shut the door. The walls were paper thin in the small trailer so I could hear her moving around and opening drawers. I also thought I heard her phone go off once or twice too but I didn’t pay it any mind.

I looked down at my lap. My dick was hard as a rock and I figured that this would be the only opportunity I was going to get to readjust myself. I stood up and shifted my rod between my legs and rearranged everything to get it as comfortable as possible. I sat down just in time as her bedroom door opened.

“Sorry about that,” she said while walking back to the couch.

She was no longer wearing the towel. She had changed into a pair of very short, loose fitting boxer shorts that she had rolled up to the point that her ass cheeks were clearly visible. Up top was a spaghetti strap shirt that did almost nothing to conceal her tits that had to at least be a D cup. She was also not wearing a bra.

“There, that’s better, “she said plopping back down onto the couch next to me and it was then that I noticed that she had a small box in her hand.

“Do you smoke,” she asked as she opened the small wooden box.

The smell of the contents hit me before the sight did. There were a number of joints in the box and she asked if I would like to share one with her.

“Sure,” I told her and she handed me the joint. I pulled out my lighter and I fired it up.

The smoke in my lungs felt like acid burning my insides. I coughed heavily for about a minute. I looked over at Sara who had a shit-eating grin on her face.

“Has it been a while?”

“Yeah, just a little bit,” I wheezed. I took another sip of my beer and I watched her hit the joint like a pro.

Ten minutes later, and one completely obliterated joint down, Sara and I were feeling right. We were both slouching on the couch and giggling about how quiet it was in the house, at least until Sara broke the silence.

“So, I’ve got a question,” she said. “I’ve got a question and it’s kinda a personal one.”

“Ok. Shoot… I’ve got nothing to hide.”

“You know Tiffany right? Tiffany Winters?”

Tiffany Winters was a fuck buddy that I had been talking to for the past two or three weeks; and by talking I mean we have both been fucking each other’s brains out. Tiffany was also Sara’s neighbor.

“Yeah, I know her. Why do you ask?”

“Have you been fucking her?

A deviant smile crept across my face and a quiet “maybe” passed through my lips.

Sara lit another joint and passed it to me. I gladly accepted it and took a hit. I coughed again but not as badly as the first time.

“Why do you want to know whether or not I have been fucking her,” I asked, wanting to know where this conversation was going.

“Because she told me something about you…” It was her turn to flash a deviant smile and her eyes locked onto mine.

“Oh, yeah… What did she tell you,” I asked, getting more and more curious and turned on by where this conversation was possibly going.

“It’s nothing bad; I promise. It’s really good actually.”

“Well then why do you tell me what she said?!”

“She said that you had a big dick. But not only that. She said that you had a big dick and you really knew how to use it!”

I couldn’t believe that she had just said that. Sara was a friend and all but I never in a million years would have imagined her and I having a conversation about the size of my cock while high as fuck. I also couldn’t believe that Tiffany actually told her all this. I don’t know why I’m surprised, I said to myself. That little slut has a big mouth anyways.

“I guess I’m an ok size. I’m not huge but I’m proud of what I’ve got.”

“Well according to Tiffany, you have good reason to be.” She took another drag off of the joint and handed it to me. I took a bigger hit this time but I didn’t cough as much. I still could believe that we were really having this fucking conversation. This could get dangerous John, I said to myself. Sara was a lonely housewife, and here I was alone with her and high as fuck.

“So John,” Sara said shyly. “Do you think that I could maybe see it?”

I nearly had a heart attack! Did she really just ask to see my cock?!

“You’re not serious right now! This is just a joke right? You’re just fucking with me!”

“No I’m not either! I’ll even let you see my tits if you whip it out for me!”

I couldn’t believe that she actually wanted to see my cock! This was Sara; my friend’s wife and here she was asking to see my cock! What’s worse is that I wanted to show it to her. It has to be the weed! It took me all of one minute to come to my decision.

“Are you sure about this,” I asked her and she said “yes” before I could even finish the question.

I shook my head and said “ok,” and I slowly pulled at the strap of my belt and freed the bar from the hole, loosening my cargo shorts. I looked up at her face and I could see that she couldn’t wait to see it. I pulled my belt from my shorts and one swift movement and threw it on the floor. After that I unbuttoned my shorts. I unzipped them slowly and finally, I lifted up my ass and pulled my shorts and my underwear down to my sandal clad feet.

My cock was fully exposed to Sara now. She stared at it hungrily. She had a look on her face that told me it had been a long time since she had seen, or enjoyed a cock like mine.

“So,” I said with a hint of confidence in my voice, “is it what you were expecting.”

Sara licked her lips.

“It’s such a pretty cock John, and I love that you shave it! How big is it?”
“It’s about 7 ½ inches long and about six inches around,” I said proudly.
Sara licked her lips at the sight of my cock and I knew what was coming next; I just wasn’t sure if I was completely ok with it.
“Can I touch it,” she asked almost demurely.
“I thought you were going to let me see your tits,” I shot back.
“Oh yeah… A deal’s a deal I guess,” and with that that, she reached back and pulled her top up over her tits and then her head giving me a full view of her chest.
Her tits were about what I was expecting them to be. They were probably DDs and they sagged a bit but I was still very eager to get my hands on them. Her nipples weren’t particularly large; maybe the size of dimes. Her areolas were about the size of silver dollars so all in all I’d say she had nice tits. I wanted to touch them but I was too nervous to ask even though she was getting ready to touch my cock which was already oozing precum.
“Can I touch it now,” she asked.
“Yes but can I touch your tits too,” I asked nervously.
“Please do!”
She was the first to move. Her hand was soft and still felt slippery from the tanning oil she had used while she was sunning herself. She started to stroke it at the base and then she would slowly move upward as if she were trying to get more precum to seep out of the head of my engorged member. Her hands felt practiced; like she knew what she was doing which, I’m sure she did. After all, she’s what, 25 or 26 maybe; and married with two kids. She better know what she was doing.
I on the other hand was not so astute in the ways of gently making a woman feel good. I quickly and roughly went for her chest and grabbed her tits as if they were bean bags. Sara quickly chastised me and told me to slow down and be easy with them. She told me to ease up on the pressure and to not pinch her nipples so hard. I did my best to follow her instructions.
We stayed like this for another few minutes or so. We were getting more and more comfortable with each other and I asked her if she would light up another joint. She said yes and she grabbed the small box, pulled one out, lit it and took a fat hit without letting go of my cock. She passed it to me and I too took a big hit. It burned again but this time I barely coughed. I was starting to get brave. My touches were becoming more and more focused. Instead of roughly squeezing her entire breasts, I was gently caressing each nipple and throwing in an occasional pinch which would elicit a moan from Sara. I must be a fast learner, I said to myself. I decided to take a gamble at that point and I leaned in and took her left nipple into my mouth and sucked it gently. Sara squirmed in pleasure but she pulled my head away. She took her hand off my cock and I instantly thought that I had fucked up.
“If you do that again, the next place we’re taking this my bedroom. Are you sure that is what you want?” I could tell by the look in her eye that she was dead serious. I didn’t answer though; at least not verbally.
I took another hit from the joint, inhaled deeply, and then I put my lips onto hers. When our lips met, Sara inhaled, taking the marijuana smoke from my lungs. She exhaled through her nostrils and we continued to kiss. Our tongues danced in each other’s mouths as our hands went back to where they were when all of this started.
“Bedroom, now,” was all she manage and I quickly follow behind her.
It took us only seconds for the two of us to be devoid of clothing. This was also my first time ever seeing Sara naked. I paused and took in her body. Her chestnut brown hair was down to her shoulders and it framed her soft face. She had brown eyes and an upturned nose that was just a little too big for her face. Her lips were pouty but not particularly plump. Her chin, like the rest of her face was round and soft looking.
My eyes continued to move down over her body. From her thin neck to her large chest I admired every inch of her. Her midsection was marked by childbirth. There was a paunch that was accompanied by stretch marks that covered medium-sized love handles. If I had to describe her with one word; that word would be “soft,” and “soft” women were fast becoming my favorite kind of woman.
My gaze finally made its way down to her sex. There was a small tuft of hair above two very plump pussy lips that already looked like they were glistening. Her thighs were much like her pussy lips; plump and inviting.
“John!” Sara hollered. I stopped my appraisal of her body and answered with a startled “what.”
“Are you just going to stand there and stare at me or are you going to come to bed and fuck me?”
I needed no more enticing so I quickly jumped on the bed and brought my lips to hers. The make out session was short-lived though because Sara desperately wanted my cock inside of her. She guided me on top of her and brought it to the entrance of her dripping pussy. She looked up at me with desperation in her eyes and she said to me in a forceful tone, “Fuck me!”
I looked down to see my cock at the entrance of her juicy cunt and in one swift motion, I pushed forward. My cock was completely engulfed by her sex in less than a second and she nearly screamed. I felt my cock hit bottom and I quickly pulled back out almost entirely.
“Oh God John, please fuck my pussy! Fuck me good baby! It’s been so long and your cock feels so good!” Sara continued speaking these words as if they were a mantra. “Fuck me John! Harder! Oh God yes right there baby! Hit it right there! It feels so good!”
I was in sensory overload. I had lost my virginity years ago but no sexual encounter I had had in the past was this intense. The way I knew my cock was making her feel made me feel like a sex God. Hearing her beg me to fuck her as hard as I could was like hymns of worship to me and I absolutely could not get enough of it. I knew that if we kept going at this pace, I wasn’t going to last very long so I tried to focus on making her cum.
“Oh my God John you’re going to make me cum already! Please don’t you dare stop fucking me John! Please let me cum John! I’m begging you! Don’t ever stop fucking me baby. It feels so good!”
Hearing Sara talk this; hearing her beg me to keep fucking her was starting to drive me over the edge. I could feel my body preparing for the onslaught that would soon be one of the most powerful orgasms of my young life. I started to feel Sara’s pussy begin to get tighter as her ensuing orgasm began trying to milk my cock. I could hear her telling me that she was cumming but I was too far gone to listen. I was in heaven.
“Oh John here it comes baby! You’re going to make me cum! Do you know how long it’s been since a man has made me cum? Do you? It’s been years! And you’re about to do it after fucking me for only five fucking minutes baby! Oh fuck, oh fuck, oh fuck! I can feel your cock getting harder John. Do you want to cum inside of me? Do you want to fill my neglected pussy up with your hot cum?”
“Yes,” was all I could muster.
“Do it baby. Fill my cunt up with your hot cum! Please do it! I know you’re close John! I know you want to and my pussy is so desperate for it. I need you cum John!”
Hearing her talk like that made me lose all control. My entire body went rigid and I emptied what felt like a gallon of cum into Sara’s cunt. Her screams sounded distant as I focused on one of the most powerful orgasms I have had ever had. It seemed to last at least an hour and when it finally subsided, I collapsed on top of Sara and she put her arms around me.
“That was absolutely amazing John! Please tell me you will fuck me again! I will do whatever you want me to do. I will be your slave, your slut; whatever you want me to be for you I will be it just please do not ever stop fucking me.”
“Well if you really mean that Sara the first thing you can do is go and get us another joint.”
“Anything for you John, and she hopped up and went into the living room of the trailer to grab the little box. As she walked to the door, I took the opportunity to admire the way her large tits and her ass bounced as she got up to get the marijuana for the two of us to share. When she walked out, I took a deep breath and put my arms behind my head and smiled.

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